ApPENDIX: OXIDATIONS OF ORGANIC COMPOUNDS LEADING TO SPECIFIC OXIDATION PRODUCTS

Examples of procedures, which are described in detail at the end of each chapter, have been collected in the following table. Organic compounds are listed vertically, oxidation products horizontally. On the cross sections one can find the page number( s) referring to the experimental procedures. When two or more procedures are available, the reader can make a proper selection. Superscript numbers (e.g., I) refer to the extended lists of pages given in the footnotes. 878 ApPENDIX

..~ E ..~ .., ~ ~ c .. ~ ..c c0 "u"' c ~ c :; .. ~ ;: .2 M C ~ u 0 C u ":; 2'" ... ~ .2 ..,.. ~ !, 0 .. <:r C ~ g c.. .. i c "~ 0 c ~ "0 '" 0 ::l .. .<: ~ u c ~ ..,"".. Co u of: 0 .;; c :: i.<: ~ I; u ~ "" ... I>- u .<: < :.: '" is u.." C is £ is -'"'" w u.." is ~ "-

Alcohols H02 Hbol

Primary 30.416. 601

Secondary

Teniary

Allylic 104.105. 832

Benzylic 416

Acelylenic 240

:I-Keto 416

Sieroid Sll H5.830

804.832. Diols 804 III

Polyols SJI 561

Lactols 528

Ethers 106 106 106 618 499

Phenols

436.735. 364.437. Monohydric 433, S62 417 602 498 804 735

Polyhydric 14K 436

Hydrocarbons

Saturated cyclic 96.466 466

101.107. 659.676. Unsaturaled 309.466 308.309 29.866 311 466.677 867

Acctylcnic 734 685.734

97.9K. Activated 99 98.360 99.100

Aromallc 618 842. &43

'102.236.240.561.830. '103. 105.237.238.416.465.830. 1105.416.465.601.832. 4364. 433. 545. 616. 735. '100.310. 360. 361. 435. 498. 867. ~ I FIByones :l> ." Amide. ~ Z C Nitriles ><

Isocyanates

Alo.'aTol)' compounds

Aminooxides

Ox azoic.

OxadialOles

I ''''"''w"' ~I I I I I I I I I I I I I I 8enzimidazoles

Oxime.

Nilrates

tLYlaromatic compounds .. .. i ;; .. I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I I ; I ; I ; I C- C dimers ~ I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I ; I Diyne. I Sulfoxides

00 Sulfone, ..... -D

Disulfide. 880 APPENDIX

::: "

~ ~ c: .; ~ c: ~ "0 c: c: ·u .;;" ~ ~ "0 .:; "" .2 ~ " 0 ~ ~ c: ~ 0 :; cr u u .2 .., ~ 0 c c u ~ 0 " u cr R i ~ ~ ~0 0 c ..c: ..c: c 0 ~ ~ 2 .;; ~ .;; "0 '" 0 N ..c: ..c: u "" .... c .., C Q. u of "0 -c ~ 0 ~ ..c: ~ U .... Q. " ,l! "'" ..c:" < ~ is """ u" is :: is ...I" L

Aldehydes 435 865

311.417. 733.865 311 Ketones 805.835

Isocyanides

Carboxylic acids 80S 236.731

o-Hydroxy 83l 237.835

Hydrazides 611

Mercaptans

Sulfides

Sulfoxides

Amines. aliphatic

Primary

Secondary

Teniary

Amincs. aromatic

Primary

Secondary

Teniary

Hydroxylamines

H ydrazines. hydrazones

107.601. Oximes 601.734 734

Enamines

Imines

Semicarbazones 601

Indoles 437

Dihydro- 1.2-oxazoles ApPENDIX 881

.; c :> .; 0 c Q. :> 0 E Q. E .~ 8 0 " I! ~ '" " ~ " e OJ OJ" ;;- ~ "2 E ~ ~ ~ 0 u "2 " c c ::: ~ u 2 E u ~ u 0 ""E ~ '0 u "";; c ~ ~ .. c ~ '0'" ::: ';::; § >," ..2 ..2 '""" ""E u <; E c :; E .,. u ~ ~ G:" Z '" " .l! i5 « ~ < « c5 c5 '" c5 i < u 0 '"-= '"-=

~J6

132 7ll

J58

J2 615.llJ

J2. Jl. 466 602

466

868 868

JI

4J6 551 238

466 834

858

J ••. 554

806.834

562

406 4Ot>

]52

238 INDEX

Acenaphthene fl-Acetoxyacrylic acid. from ethene. 494 to acenaphthenone. 57 Acetoxybenzylphenyl ketone. from benzylphenyl to acenaphthenequinone. 57. 297 ketone. 786 to 1-acetoxyacenaphthene. 757 1-Acetoxy-2-butanone. from methyl ethyl ketone. Acenaphthenequinone. from acenaphthene. 57, 297 786 Acenaphthenone. from acenaphthene, 57 a-Acetoxybutyrophenone. from butyrophenone. 786 Acetaldehyde 7-Acetoxycholesteryl acetate. from cholesteryl from alcohol using cerium IV, 577 acetate. 80 I from ethylene, 471 a-Acetoxycycloheptanone. from cycloheptanone. from lactic acid. 820 786 Acetaldehyde dialkylacetal. from ethylene. 475 a-Acetoxycyclohexanone. from cyciohexanone. 786 Acetals. from alcohols with PdCI2 • 496 2-Acetoxycyclohexanone. from cyclohexanone. 805 Acetic anhydride 3-Acetoxycyclohexene. from cyclohexene. 747 to acetoxyacetic acid, 306 a-Acetoxycyclopentanone. from cyclopentanone. to succinic anhydride, 306 786 Acetone 3a-Acetoxy-4.4-dimethyl-5a-androstan-2-one. from to a-acetoxyacetone, 786 4.4-dimethyl-5a-androstan-2-one. 786 to a,a' -diacetoxyacetone. 786 2-Acetoxy-2.6-dimethylcyclohexa-3.5-dienone. from 2.3-dimethylbutane-2.3-diol. 820 from 2.6-xylenol. 821 to 2.5-hexanedione. 306 2-Acetoxy-1.2-diphenylethanones. from a-phenyl• from 2-methyl-2-hydroxypropionic acid. 820 cinnamic acids. 293 from pinacol. 780 Acetoxylation of carbonyl compounds by LTA. 786 from 2-propanol. 776 9.IO-bis(Acetoxymethyl)anthracene. from 9.10- Acetone p-bromophenylhydrazone. to 2-(p-bromo• dimethyl anthracene. 757 phenylaxo)-2-acetoxypropane. 801 Acetoxymethylenephenylsulfide. from thioanisole Acetone phenylhydrazone using Mn(OAch. 292 to 2-acetoxy-2-phenylazopropane. 806 l-Acetoxy-2-methylnaphthalene. from 2-methyl• to 2-phenylazo-2-acetoxypropane. 801 naphthalene. 297 2-Acetonyl-cyclohexanone. from isopropenyl• I-Acetoxy-6-methoxytetralin. from 6-methoxy• acetate. cyclohexanone, and Mn(OAch. 311 tetralin. 757. 802 Acetophenone 17/3-Acetoxy-3-oxo-5a-androst-l-ene. to 17/3- from acetophenone benzoylhydrazone. 397 hydroxy-I,3-seco-2-nor-5a-androstane-l.3- to a-acetoxyacetophenone. 786 dioic acid. 466 from ethylbenzene. 858 9-Acetoxyphenanthrene. from phenanthrene. 297 to methyl phenylacetate. 715 2-Acetoxy-2-phenylazopropane, from acetone phen• from 2-phenylpropionaldehyde. 429 ylhydrazone. 806 from styrene. 853 cis-2-Acetoxy-l-phenylcyclohexanol. from I-phen• Acetophenones ylcyclohexene. 824 to methyl a-methoxyarylacetates. 717 I-Acetoxy-2-phenyl-2-propanol. from a-methyl• to a-nitrato ketones. using TI(N03h, 718 styrene. 824 oxidation of. with TUNO])" 733 I-Acetoxy-2-phenylpropan-2-o1. from 2-phenylpro• Acetophenone benzoylhydrazone. to acetophenone. pene, 824 397 cis-2-Acetoxy-pin-3-ene. from a-pinene. 749 I-Acetoxyacenaphthene. from acenaphthene. 757 3fl-Acetoxy-5a-pregnane-Il.12-dione. to 3/3.21- Acetoxyacetic acid. from acetic anhydride, 306 diacetoxy-5a-pregnane-Il.20-dione. 786 a-Acetoxyacetone. from acetone. 786 17-Acetoxytesterone. to A-nor-2a-methoxycar• a-Acetoxyacetophenone. from acetophenone. 786 bonyl-3-androstan-17/3-yl acetate. 733 883 884 INDEX

l-Acetoxytetralin. from tetralin. 757 Alcohol 2-Acetoxy-a-tetralone. from a-tctralone. 786 allyl 2-Acetoxy-2.4 .6-tri-t-buty lcyclohexa-3 .5-dienone. to acrylic acid. 378 from 2.4.6-tri-t-butylphenol. 804 10 allyl aldehydes. 379 4-Acetoxy -2.4. 6-tri-t-buty lcyclohexa-2 .5-dienone. cinnamyl. to cinnamlC acid. 378 from 2.4.6-tri-t-butylphenol. 804 furfuryl. to furfural. 379 1-(4-Acetoxy-2.6.6-trimethyl-2-cyclohexen-l-yl )- a-furfuryl. to a-furoic acid. 378 2(E)-buten-l-one. preparation of. 237 propargyl. to propiolic acid. 378 N-Acetyl-N' -acylhydrazones. from monosubstituted Alcohols hydrazones. 800 to aceta Is with PdCI~. 496 Acetylenes acetylenic heterocyclic. oxidative coupling of. 426 to carbonyl compounds. 379 oxidative coupling of. 438-439 oxidation of in the presence of amines. using Acetylenic ketones. from alkynes. 52 MnO~. 149 N-Acetyl-2-methylpiperidine. to N-acetyl-2-methyl• a.l3-unsaturated. oxidation of. using MnO~. piperidone, 455 144 N-Acetyl-2-methylpiperidone. from N-acetyl-2- to aldehydes methylpiperidine. 455 using 2.2-bipyridinium chlorochromate. 78 R-( + )-N-Acetyl-2-phenylpynulidine. to R-( + )-N• using chromylchloride. 73 acetyl-5-phenyl-2-pynulidone. 455 with PdCI~. 496 N-Acetyl-2-phenylpynulidine. to N-acetyl-5-phenyl- using pyridinium chlorochromate. 77 2-pynulidinone. 466 alicyclic. cleavage of. using Ce(lV). 604 N-Acetyl-5-phenyl-2-pynulidinone. from N-acetyl- aliphatic. cleavage of. using Ce(lV). 604 2-phenylpynulidine. 466 allyl. from olefins. 851 R-( + )-N-Acetyl-5-phenyl-2-pynulidonc. from R• allylic. oxidation of by PdCI,. 476 (+ )-N-acetyl-2-phenylpynulidine. 455 benzylic. oxidation of. using MnO~. 157 Acids benzylic. to carboxylic acids. 378 from benzyl ethers. 83 to carbonates with CO and PdCI~. 497 dimerization of. 860 to carbonyl compounds from primary alcohols using POC. 77. 104

using PdS04 , 497 to carboxylic acids. using POC. 77 using RuO •• 450 to chlorocarbonates with CO and PdCI~. 497 a.l3-unsaturated. to carbonyl compounds, 476 cinnamyl. to cinnamyl aldehydes. 379 Acridine. to acridone. 591 cyclopropane. nonconjugated. oxidation of. using Acridone. from acridine. 591 Mn02.142 Acridones. from 2-aminobenzphenones. 291 dimerization of. 860 Acrolein. to acrylic acid, 849 1,l-disubstituted a-allenic Acrylic acid to a-allenic aldehydes. 379 from acrolein. 849 to a-allenic amides. 379 from allyl alcohol. 378 to a-allenic ketones. 379 from ethene. 494 heterocyclic. oxidation of. using MnO~. 167 Activated C-H bonds. hydroxylation of. 857 a-keto-. to carbonyl compounds. 379 Activated C-H-containing compounds. oxidation to ketones of. 409 using 2.2-bipyridinium chlorochromate. 78 Acylazocarboxylates. to lactams. 224 using pyridinium chlorochromate. 77 Acylbenzylcyanides. oxidation of. 428 oxidation of, 378 a-(Acylmethyl)-a./3-enones. from cyclobutanols. using ee(IV). 604 578 using OsO•. 647 Acyloins. from dialkyl acetylenes. 720 using pyridinium chlorochromate. 74 Adamantan-2-01. to 2-oxohomoadamantan-3-one. oxidative cyc1ization of. 607 601 phthalyl. oxidation of. using MnO~. 159 2-Adamantanol. to adamantanone. 577 primary Adamantanone. from 2-adamantanol. 577 a.l3-unsaturated. oxidation of. using Mn02' cis-2-( I-Adamantylamino )cyclohexanol. from 128 cyclohexene. 682 oxidation of. 380-381 Adipaldehyde oxidation of. using chromic acid. 70 from cyclohexene. 458 to carbonyl compounds. 79 using OsO.!sodium periodate. 677 primary to acids

from cis-cyclohexane-1.2-diol. 384 using PdS04 • 497

Adipic acid. from cyclohexane. 466 using Ru04 • 450 INDEX 885

Alcohols (cont.) Alkenes (cont.) primary to aldehydes. 382 to oxiranes. using chromyl acetate. 60 using Ag 2CO,. 507. 510-518 oxyamination of. 642. 643 using RuO •• 450 Alkoxybenzimldazolones. oxidation of. 590 primary to carboxylic acids. 378 p-Alkoxycinnamic acids. to 2.6-diaryl-3.7-dioxabi• propargylic. oxidative cleavage of. using cycll'(3.3 .OJoctane-4. 8-diones. 706 Ag 2CO,.556 3-Alkoxy-2.6-disubstituted benzoquinones. from saturated aliphatic. oxidation of. using MnO,. 2.6-disubstituted phenols. 430 169 Alkyl aryl acetylenes. to methyl-ct-alkylaryl- secondary acetates. 720 to ketones. 382 Alkyl benzenes. to aliphatic carboxylic acids. 461 to ketones by PdSO •. 497 Alkyl ferrocenes. oxidation of. using MnO,. 202 to ketones. using Ag,CO,. 507. 520-523 4-Alkyl-4-alkoxycyclohexa-2.5-dienones. from to ketones. using RuO •. 450 phenols. 735 ct.p-unsaturated. oxidation of. using MnO,. 128. N-Alkyl-4-cyanopyndinium salts. oxidation of. 129 585 secondary alkynic. oxidation of. using MnO,. 4-Alkyl-2.6-di-butylphenols 146 to p-benzoquinones. 430 to tetrahydrofurans. using L T A. 802 to quinolideperoxides. 430 unsaturated. oxidative cleavage of. 378 2.5-Alkyl-I.4-dimethoxybenzens. oxidative demeth• cis-unsaturated. oxidation of. using MnO,. 131 ylation of. 588 trans-unsaturated. oxidation of. using MnO,. 131 N-Alkyl-2 .6-dipheny 1-4-piperidone-3 .5-dicarboxy lic unsaturated steroid. oxidation of. using MnO,. esters. dehydrogenation of. 581 153 4-Alkyl-4-methoxycyclohexa-2.5-dienones. from 4- Aldazine bis-N-oxides. from aldoximes. 399 alkylphenols. 726 Aldehyde. 4-Methylpent-2.3-diene-I-ol. from 4- Alkylarenes. oxidation of. 619 Methylpent-2.3-diene-I-ol. 379 ct-Alkylarylacetic ester. preparation of. 717 Aldehyde monohydrazones. oxidation of. 394 Alkylarylacetylenes. to ct-alkylarylacetates. 734 Aldehydes ct-Alkylarylacetylenes. from alkylarylacetylenes. from alcohols 734 using chromylchloride. 73 Alkylarylmethanols. oxidation of. using Ce(lV). using 2.2-bipyridinium chlorochromate. 78 606 using pyridinium chlorochromate. 77 Alkylbenzenes. oxidation of ct-allenic. from I.I-disubstituted ct-allenic alco- using C. 336 hols. 379 using aqueous sodium dichromate. 55 to methyl esters. using Ag,CO,. 545 using chromic acid. 54 from ct-oletins. 475 using chromyl acetate. 55 oxidation of. using 050•. 649 using chromyl chloride. 56 with PdCI,. 496 3-Alkylidene grisens. from grisen-3-ones. 458 from primary alcohols. 382 Alkylimidoosmium compounds. to amino alcohols. using Ag,CO,. 507. 510-518 682 using RuO •. 450 4-Alkylphenols. to 4-alkyl-4-methoxycyclohexa- from semicarbazones. 722 2.5-dienones. 726 ct.p-unsaturated. oxidation of. using MnO,. 143 Alkynes Alditols. synthesis of. 174 to acetylenic ketones. 52 Aldoximes. to aldazine bis-N-oxides. 399 to carboll:ylic acids. 460 Alicyclic alcohols. oxidation of. 769 to ct-diketones. 460 Aliphatic C-H bonds. hydroxylation of. 856 functionalized. to allenes. 596 Aliphatic ketoximes. to ct-nitroso-ct-acetoxyalkanes. oll:idation of. using 050•. 645 798 to substituted benzenes. 343 Alkaloids. oxidation of. using MnO,. 157 Alkynoic esters. from 3-substituted 5-pyrazolones. Alkanes. oxidation of. using C. 336 using Tl(NO,h. 720 Alkanols. primary. to tetrahydrofuran. 579 2-Alkynoic esters. from 5-pyrazolones. 734 Alkenes Allenes. from functionalized alkynes. 596 to cis-diols. 637. 672-676 Allenic esters. from 3,4-disubstituted 5-pyrazo- cis-hydroxylation of. 672-676 lones. 721 long chain. oxidation of. 459 Allylalcohol. to glycerol. 642 oxidation of. 676 Allyl aldehydes. from allyl alcohols. 379 using chloramine-TIOsO •. 644 Allyl phenyl ether. to 3-hydroxychromane. 713 using chromium oxidants. 61 Allyl trimethylsilyl ethers. epoxidation of. 17 886 INDEX

2-Allyl-3-methyl-5.6-dimethoxybenzoquinone Androstane-3/3.5a.6/3-triol. oxidation of. 534 from 2.3A.5-tetramethoxy-6-allyltoluene. 616- 5a-Androstane-4/3.17/3-diol 17-propionate. to 4- 617 oxo-5a-androstan-17/3-01 propionate. 776 from 2.3A.5-tetramethoxy-6-geranyltoluene. 5a-Androstane-3/3.613-17/3-triol 3.17-diacetate. from 616-617 6-oxo-5a-androstane-3/3 .1713-diol. 3.1713-01- 2-Allyl-3-methyl-IA-naphthoquinone. from 104- diacetate. 776 dimethoxy-2-allyl-3-methylnaphthalene. Aniline. to azobenzene. 385 616-617 Anilines Allylic C-H bonds. hydroxylation of. 857 to azobenzenes. 858 Amides using Ag2CO~. 551 a-allenic. from l.I-disubstituted a-allenic alco• to benzoquinones. 88 hols.379 to nitrobenzenes. 859 substituted. to substituted imides by RuO •• 453 o-substituted. oxidative cyclization of. using a./3-unsaturated. to carbonyl compounds. 476 Mn02.208 Amine oxides. from teniary amines. 26 Anisaldehyde Amines from anisyla1cohol. 832 aliphatic. oxidation of. using Ag2CO). 550 from p-methoxytoluene. 296 aromatic. primary Anisil. from anisoin. 826 to azo compounds. 385 Anisoin. to anisil. 826 to azo compounds. via LTA oxidation. 796 Anisylalcohol. to anisaldehyde. 832 dehydrogenation of. using Mn02. 210 Anthracene dimerization of. 860 to anthraquinone. 296. 855 to nitroxyl radicals. 858 to 9.10-anthraquinone. 14 oxidation of. using Mn02' 204. 205 to cis-9 .1O-diacetolty-9.1 O-dihydroanthracene. primary. oxidation of. 391 using LTA. 755 using MN02• 207 10Irans-9.IO-diacetoxy-9.IO-dihydroanthracene. primary. to oximes. 858 using LTA. 755 secondary. to nitrones. 858 oxidation of. 639 secondary. oxidation of. 393 1.4.9.IO-Anthradiquinone. from quinizarin. 616- using MN02• 207 617 secondary. to hydroxylamines. 858 Anthraquinone secondary to tetrasubstituted hydrazines. 390 from anthracene. 296. 855 teniary. to fonnamides. 212 from anthrone. 591 teniary. to N-oxides. 858 9.IO-Anthraquinone Amino alcohols. from alkylimidoosmium from anthracene. 14 compounds. 682 fonnation of. 590 2-Aminobenzophenones. to acridones. 291 Anthrone. to antraquinone. 591 I-Aminobenzotriazole. to benzyne. 409 Aporphines. from benzyltetrahydroisoquinolines. 22 a-Aminoketones D-Arabinose. from d-mannose. 780 to a-diketones. 212 L-Arabinose. to L-glycerinaldehyde. 780 to pyrazines. 212 Aromatic 1.2-amines. to cis-muconitriles. 796 2-Aminomethyl-5-chloro-l-methy 1-3-phenylindolc. Aromatic C-H bonds. hydroxylation of. 857 to 7-chloro-1.3-dihydro-l-methyl-5-phenyl- Aromatic compounds 2H-I.4-benzodiazepin-2-one. 89 dehydrodimerization of using Tl(lII). 697 Aminonitriles. to cyanoanils. 217 oxidative carboxymethylation of using o-Aminophenol. to o-quinonemonoanil. 545 Mn(OAch. 287-288 n-Amyl iodide. from n-hexanoic acid. 794 oxidative coupling of by Pd". 488 a-Amyrin. to a-amyrone. 831 Aromatic hydrocarbons. nitromethylation of. 289 a-Amyrone. from a-amyrin. 831 Aromatic hydroxylation. 855 Androst-4-ene-3-17-dione. from testosterone. 830 Aromatic methyl groups. oxidation of. 857 Androstan-17-one. from pregnan-17a.20/3-diol. 519 Aromatic nuclei. destruction of by RuO •• 461 Androstan-3 .17 -dione. from 5a-androstan-3a-ol-17- Aromatic rings. hydroxylation of. 857 one. 450 Aromatics. oxidative carbonylation of. 496 5a-Androstan-3.17-dione. 5a-androstan-3-o1-17- Aryl malonaldehydic acid dimethyl acetals. from one. 450 methyl cinnamate. 733 5a-Androstan-3-01-17-one. to 5a-androstan-3.17- w-Aryl n-alkanols. oxidation of. using TI(III). 706 dione.450 Aryl-I.2-diaminoimmidazoles. ring transfonnation 5a-Androstan-3a-oI-17 -one. to 5a-androstan-3 .17- of. 211 dione.450 Arylacetaldehydes. from styrenes. 712 INDEX 887

Arylcyanoacetamides. oxidation of. 428 Benzene (cont.) Arylcyanoacetic esters, oxidation of, 428 hydroxylation of. 855 Arylcyclopropanes to phenylacetate. 499 cleavage of, 620 Benzeneamine. to nitrobenzene, 12 ring opening of, 593 Benzenemethanols. oxidation of. using Mn02' 160 Aryldiazomethanes Benzenes, substituted, from alkynes. 343 to cis-stilbenes, 586 Benzhydrol. to benzophenone. 72 to trans-stilbenes. 586 Benzhydryl acetate, from diphenylmethane. 757 Aryldiazonium ions, from arylhydrdzines. 797 Benzil Arylhydrazines. to aryldiazonium ions, 797 from benzoin, 776, 826 Arylmalondialdehyde tetramethyl acetals, from from diphenylacetylene. 460. 645, 686 cinnamaldehydes, 715 Benzil bishydrazone, to diphenylacetylene. 395 L-Ascorbic acid, from L-gulono-'Y-Iactone. 849 Benzil monohydrazone, oxidation of, 395 trans-Aurones. from 2' -hydroxychalcones, 292 Benzilic acid hydrazide, to benzophenone. 583 a-Azido-/3-nitratoalkanes. synthesis of. 627 Benzils Azines, oxidative cleavage of, using Mn02' 220 from diaryl acetylenes. 720. 733 Azirines. to 2-styrylindoles. 356 Benzimidazoles. from N-benzylidine-o-phenylenedi• Azo compounds amines.405 from aromatic primary amines, 385 Benzo(b)furan. oxidation of. 483 from N ,N' -disubstituted hydrazines. 797 Benzoid acid

from hydrazines, using Ag 2COJ , 553 from benzaldehyde, 384. 452 from primary aromatic amines, via LTA oxida• from mandelic acid. 384 tion, 796 from phenylacetonitrile. 407 Azobenzene from phenylacetylene, 686 from aniline. 385 from toluene. 407 from hydrazobenzene. 834 Benzoin Azobenzenes to benzaldehyde, 820 from anilines. 858 to benzil. 776, 826 using Ag2CO,. 551 Benzoins. splitting of. using Ce(IV), 608 2,2' -Azobenzothiazole, from 2-hydrazinobenzothia• Benzonitrile zole, 392 from benzylamine. 385 Azopyrazoles. from 1,2-diketone bisphenylhydra• to 2-phenylpyridine, 361 zone, 396 Benzophenone Azoxybcnzene, from phenyl hydroxylamine. 392 from benzhydrol. 72 from benzil monohydrazone. 395 from benzilic acid hydrazide, 583 Benzlalanthracene. to benzanthraquinone. 297 from benzophenone phenylhydrazone, 395 Benzaldehyde from diphenylacetaldehyde, 429 to benzoic acid. 384,452 from diphenylglycolic acid, 820 from benzoin. 820 to diphenylmethane. 407 from benzyl alcohol. 450. 465. 832 from diphenylmethanol, 105 from benzyl alcohol using Mn(OAch, 290 Benzophenone hydrazone. to diphenyldiazo• from cinnamic acid, 293 methane, 394. 834 from hydrobenzoin, 820 Benzophenone phenylhydrazone. oxidation of. 395 from meso-hydrobenzoin. 832 p-Benzoquinone. from IA-dimethoxybenzene. 616- from mandelic acid, 384. 820 617 from toluene, 855 lA-Benzoquinone Benzaldehyde benzoylhydrazone. oxidation of, 396 from hydroquinone, 14 Benzaldehyde oxime. to 3.5-diphenyl-1.2.4-oxadi• from 4-hydroxybenzylalcohol, 822 azole, 562 p-Benzoquinone. from hydroquinone. 616-617. 725 Benzaldehyde phenylhydrazone. oxidative C-C Benzoquinones coupling of, 395 from anilines. 88 Benzanilide. from N-benzoyl-N-phenylhydroxyl- from hydroquinones, 427 amine. 394 oxygenation of phenols, 441 Benzanilides, from benzylidine aniline. 92 from phenols. 364 Benzanthraquinone. from benzlalanthracene. 297 o-Benzoquinones. from catechols. 543 Benzene using Ag2COJ • 547 to biphenyl, 489 p-Benzoquinones from cyclohexene. 477 from 4-alkyl-2,6-dibutylphenols, 430 888 INDEX p-Benzoquinones (cont.) Biacetyl bisbenzoylhydrazone. oxidation of. 397 from hydroquinones. 543 Biaryls. substituted. from p-methoxytoluene. 295 using A2CO~. 545 Bibenzyls. cleavage of. 620 from phenols. 725 9.9'-Bicarbazole. from carbazole. 390 1.4-Benzoquinones. from hydroquinones. 364 Bicyclolx.y.zJalkan-2-0Is. cleavage of. 578 Benzothiazole. from 2-hydrazinobenzothiazole. 392 Bicyclohexyl-2.2'-dione. to cyclohexanone. 385 2.2' -Benzothiazolyl. from 2-hydrazinobenzothia- (+ HIS.5S)-Bicyclo[3.2.I IJ-2-octanone. from C+)• zole.392 (ISAR)-2-methylenenorbomane. 731 Benzoxazoles. from o-(benzylideneamino)phenols. Bicyclo[4.2.0Jota-2.4-diene-7.8-diol. from cyclooc- 399 tatetraene. 752 N-Benzoyl-N-phenylhydroxylamine. to benzanilide. Bifuryl. from furan. 489 394 Bimesityl. from mesitylene. 593 o-Benzoylbenzoic acid. from 3-hydroxyflavone. 437 Biphenyl Benzoylhydrazones. oxidation of. 400-404 from benzene. 489 Benzoylhydroxylamine. to N.O-dibenzoylhydroxyl- from benzophenone phenylhydrazone. 395 amine. 394 Bipyrazolines. from chalcone phenylhydrazones. I-Benzoylindole. oxidation of. 490 395 3-Benzoyloxy-I-butene. from 2-butene. 856 Bisazoalkenes. from 1.2-diketone bisphenylhydra• Benzoyloxy-p-xylene. from p-xylene. 868 zone. 395 7-Benzoyloxynorbomadiene. from norbomadiene. 1.3-Bis-[a-diazobenzyIJbenzene. preparation of. 855 239 Benzyl acetate. from phenylacetic acid using 1.2-BisI2-formyl-propyl-(2)-J-benzene from cis- MnCOAc).. 293 1.1.4.4-tetramethyltetraline-2.3-diol. 780 Benzyl acetate. from toluene. 757 1.5-Bis-chydroxymethyl)cyclooctene. to l-formyl-5- Benzyl alcohol (hydroxymethy llcyclooctene. 141 to benzaldehyde. 450. 465. 832 1,8-Bis-(hydroxymethyl)naphthalene. to I-oxo• to benzaldehyde. using MnCOAc),. 290 IH.3H-naphtho[ 1.8-cdJpyran. 140 Benzyl alcohols. oxidation of. 601 2.6-Bis-C3.4.5-trimethoxyphenyl)3.7-dioxabi• Benzylaldehyde. from benzyl alcohol. 465 cycloI3.3.0Ioctane-4.8.dione. from 3.4.5- Benzylamine. to benzonitrile. 385 trimethoxycinnamic acid. 731 N-Benzylamines. to benzylidineanilines. 390 Bishydrazones. to triazoles. 396 Benzylchloride. from phenylacetic acid. 794 Bisnor-S. from norbomadiene. 342 -Renzy I ethers 1.2-Bisphenylazopropylene. from methylglyoxal to acids. 83 bisphenylhydrazone. 396 to esters. 83 Bisphenylhydrazone. from glyoxal bisphenylhydra- to ketones. 83 zone. 396 Benzylacetate. from phenylacetic acid using 4,4'-Bitolyl. preparation of. 490 MnCOAch. 293 Bitolyls. from toluene. 499 N-Benzyl-3-ethylpiperidine. oxidation of. 456 Bleomycin A2. from phleomycin A2. 409 N-Benzylhydroxylamine. to a-nitrosotoluene. 392 o-Bromobenzoic acid. from o-bromotoluene. 360 Benzylic alcohols. primary. oxidation of. 577 E-2-Bromo-2' -nitrostilbene. 486 n-CBenzylideneamino)phenols. to benzoxazoles. 399 2-( p-Bromopheny lazo )-2-acetoxypropane. from Benzylidine aniline. to benzanilides. 92 acetone p-bromophenylhydrazone. 801 N-Benzylidine-o-phenylenediamines. to benzimida- o-Bromotoluene. to o-bromobenzoic acid. 360 zoles.405 4-Bromoveratrole. to 2.2'-dibromo-4.4'.5.5'-tetra• Benzylidineanilines. from N-benzylamines. 390 methoxybiphenyl. 729 N-Benzylmorpholines. oxidation of by RuO •• 456 l.l-Butadiynylenedicyclohexanol. from I-ethynyl• 2-Benzyloxy-2' .4' -bisCmethoxymethoxy)-4-me- cyclohexanol. 431 thoxychalcone. to 2' -benzyloxy-7-hydroxy- Butanal. from I-butanol. 776 4'-methoxyisoftavone. 732 I-Butanol 2' -Benzyloxy-7-hydroxy-4' -methoxyisoftavone. to butanal. 776 from 2' -benzyloxy-2' .4' -bisCmethoxy• to tetrahydrofuran. 769 methoxy)-4-methoxychalcone. 732 2-Butanone phenylhydrazone. to 2-phenylazo-2- Benzylphenyl ketone. to acetoxybenzylphenyl acetoxybutane. 80 I ketone. 786 2-Butene. to 3-benzoyloxy-l-butene. 856 Benzyltetrahydroisoquinolines. to aporphines. 22 cis-But-2-ene. oxidation of. 494 2-Benzyl-tetrahydrofuran. from 5-phenyl-l• lrans-But-2-ene. oxidation of. 494 pentanol.769 7-1-Butoxynorbomadiene. from norbomadiene. Benzyne. from I-aminobenzotriazole. 409 855 INDEX 889

I-Butyl-aceto1tymethylenephenylsulfide. from 1- -y-Butyrolactones. from olefins by oxidative addition butyl-p-tolylsulfide. 292 of carboxylic acids. 266 cis-2-(len-Butylamino)cyclohe1tanol. from cyclo• Butyrophenone. to a-acetoxybutyrophenone. 786 he1tene.682 2-lert-Butylamino-l-phenyl cycloheunol. from 1- CH-bonds. activated. acetoxylation of. 855 phenylcyclohe1tene.682 Camphene. reaction of. 749 I-Butylbenzoquinone. from I-butylhydroquinone. e-Caprolactone. from cyclohexanone. 849 616-617 Carbazole 2-I-Butylbenzoquinone to 9.9'-bicarbazole. 390 from 2-I-butyl-4-metho1typhenol. 616-617 to 9.3' .9' .9 "-tetracarbazole. 390 from 3-I-butyl-4-dimethylaminophenol. 616-617 Carbazoles. oxidation of. using MnO~. 228 from 3-r-butyl-4-metho1typhenol. 616-617 Carboalkylation with carboalkoxymercury r-Butyl-p-benzoquinone. from t-butyl-hydroquinone. compounds. 500 427.433 Carbohydrates 4-t-Butyl-o-benzoquinone. from 4-t-butylcatechol. degradation of. using Ag 2CO,. 544 616-617 oxidation of. using MnO~. 172 Butyl butyrate. from n-butyl ether. 452 regiospecific oxidation of. using Ag2CO,. 543 i-Butyl chloride. from n-valeric acid. 794 I-Carbomethoxy-2-endo-carbomethoxybi• n-Butyl chloride. from n-valeric acid. 794 cyclo(2.2.2]octane-5.6-endodicarboxylic 4-t-Butylcatechol. to 4-t-butyl-o-benzoquinone. acid. to dimethyl bicyclo[2.2.2]oct-5-ene• 616-617 l.exo-2-dicarboxylate. 805 2-iso-Butylcyclopentanone. from isobutylene. Carbonates. from alcohols and CO and PdCI~. 497 cyclopentanone and Mn(OAch. 310 Carbonyl compounds ::!.6-Butyl-p-cresol. to 2.6-di-t-butyl-4-hydro1ty-4- from acetylenic alcohols. 379 methylcyclohexa-2.5-dienone. 436 from alcohols. using PDC. 77. 104 3-t-Butyl-4-dimethylaminophenol. to 2-t-butyl• from a-ketoalcohols. 379 benzoquinone. 616-617 oxidation of. 388-389 n-Butyl ether. to butyl butyrate. 452 using Ce(IV). 608 r-Butylhydroquinone from primary alcohols. 79 to I-butylbenzoquinone. 616-617 from secondary alcohols. 79 to t-butyl-p-benzoquinone. 433 Carboxyl compounds. dethioacetalization of. 602 10 2-t-butyl-6-hydroxy-p-benzoquinone. 433 Carboxylic acid hydrazides 2-t-Bulyl-6-hydroxy-p-benzoquinone. from r-butyl• hydrolysis of. 602 hydroquinone. 433 oxidation of. 611 2-r-Butyl-4-methoxyphenol. to 2-r-butylbenzoqui• Carboxylic acids none. 616-617 from alcohols. using PDC. 77 3-I-Butyl-4-melhoxyphenol. to 2-I-butylbenzoqui• aliphatic. from alkyl benzenes. 461 none. 616-617 from alkynes. 460 I-Butylphenylketone. from t-bulylphenylmelhanol. from benzylic alcohols. 378 833 oxidative addition of. to olefins. 269 r-Butylphenylmelhanol from primary alcohols. 378. 380-381 to t-butylphenylketone. 833 Cardenolide steroids. glycosidation of. using oxidation of by triphenylbismuthcarbonate. 828 Ag2CO).561 2-t-Bulyl-6-phenylphenol. to 3.3' -di-t-bulyl-5.5'• Carotenoid diophenols. o1tidative ring contraction diphenyldiphenoquinone. 433 in. 187 3-ten-Butyl-3-phenylpropionic acid. to dimethyl• Carveol. to carvone. 103 ten-butyl-succinate. 465 (-)-Carveol. to carvone. 832 3-rert-Bulyl-3-(i' .2' .3' .4' -telrahydro-5' -naph• d-Carvomenthene. oxidation of by Mn(OAc),. 301 thyl)propionic acid. to dimethyl-ten-bulyl• Carvone succinate. 465 from (-)-carveol. 832 I-Butyl-p-Iolylsulfide. to t-bulyl-acetoxymethylene• from carveol. 103 phenylsulfide. 292 Catechol iso-Butyraldehyde. oxidative decarbonylation of. oxidative cleavage of. 429 429 to cis.cis-muconic acid. 383 i-Bulyric acid. to i-propyl chloride. 794 to monomethyl cis.cis-muconate. 436 Butyric acid. to propene. 861 Catechols Butyroin. 10 octane-4.5-dione. 826 to o-benzoquinones. 543 BUlyrolactam to succinimide. 453 using Ag2CO,. 547 Butyrolactone. from tetrahydrofuran. 452 o1tidative cleavage of. 441 890 INDEX

Chalcone dimethyl acetal. to 2.3-diphenyl-3-me• 2-Cholestanone. from 2-hydroxymethyl-5a• thoxypropanoate. 714 cholestan-2-01. 780 Chalcone ketals. to methyl 2.3-diaryl-3-methoxy• S-Cholesten-7-one-3/3-o1 acetate. from cholesteryl propanoates. 733 acetate. 97 Chalcone phenylhydrazones A4 -Cholestene-3 .6-dione. from .0. '-cholestenone. to bipyrazolines. 395 428.435 to pyrazoles. 395 t.'-Cholestenone. to .0. 4-cholestene-3.6-dione. 428.

Chalcones. using TI(N03h. 732 435 Chlorins. oxidation of using TI(III). 708 Cholesteryl acetate p-Chlorobenzaldehyde. to p-chlorobenzamide. 385 to 7-acetoxycholesteryl acetate. 80 I p-Chlorobenzamide. from chlorobenzaldehyde. 385 to 5-cholesten-7-one-3/3-01 acetate. 97 Chlorocarbonates. from alcohols with CO and Chroman. from 3-phenyl-l-propanol. 580

PdC1 2.497 4-Chromanone. from 3-phenyl-1-propanol. 580 Chlorocatechol. to chloromuconate, 429 Chromone. from 3-phenyl-l-propanol. 580 a-Chlorocyclodocedanone. from cyclododecene. Cinnamaldehyde 101 from cinnamyl alcohol. 104. 832 7-Chloro-I.3-dihydro-I-methyl-5-phenyl-2H-IA• from cinnamyl alcohol. using 2.2' -bipyridinium benzodiazepin-2-one. from 2-aminomethyl- chlorochromate. 104 5-chloro-I-methyl-3-phenylindole, 89 Cinnamaldehydes. to arylmalondialdehyde tetra• 5-Chloro-3/3.6/3-dihydroxy-5a-androstan-17-one 3- methy I acetals. 715 acetate. oxidation of. 803 Cinnamic acid /3-Chloroethylacetate. from ethylene. 473 to benzaldehyde. 293 Chloroform. to hexachloroethane. 410 from cinnamyl alcohol. 378 4-Chlorophenyl methyl sulfide. to 4-chlorophenyl to formaldehyde. 293 methyl sulfoxide. 32 Cinnamic acids. to 2.6-diaryl-3.7-dioxabi• 4-Chlorophenyl methyl sulfoxide. from 4-chloro• cyclo[3.3.0Joctane-4.8.diones.731 phenyl methyl sulfide. 32 Cinnamyl alcohol p-Chlorotoluene. oxidation of by Mn(OAch. 299 to cinnamaldehyde. 104. 832 5a-Cholest-8(14)-ene-3/3.70<-diol-15-one. from 5a• using 2.2' -bi-pyridinium chlorochromate. 104 cholest-8-(I4 )-ene-3/3,7 a .15a-triol, 102 Cinnamyl aldehydes. from cinnamyl alcohols. 379 Cholest-4-en-3/3-01 Citral. from geraniol. 379 to cholest-4-en-3-one. 832 Citronellal, from citronellol. 102 oxidation of by triphenyl bismuthcarbonate. 827 Citronellol Cholest-I-en-3/3-01. to cholest-I-en-3-one. 832 to citronellal. 102 Cholest-I-en-3-one. from cholest-I-en-3/3-01. 832 to 4-methyl-2-( I-i-butenyl)-tetrahydrofuran. 769 Cholest-4-en-3-one, from cholest-4-en-3/3-01. 832 Codeine. to 14-hydroxycodeinone. 157 5a-Cholest-8-(l4 )-ene-3/3. 7 a .15a-triol. to 5a- p-Cresol. to 4-hydroperoxy-4-methylcyclohexa-2.5- cholest-8(14 )-ene-3/3.7 a-diol-15-one. 102 dione, 626 Cholesta-2.4-diene. oxidation of by RuO •. 460 Cresol acetates 5.7-Cholestadiene. to 5-hydroxy-6-oxo-7.8-epoxy• from toluene. 499 cholestane. 460 from p-tolylmercuric acetate. 499 Cholestan-36-acetoxy-5a.6/3-diol. to cholestan-3{:l• Crotonaldehyde from crotylalcohol. 832 acetoxy-5a-ol-6-one. 450 Crotonic acid Cholestan-3/3-acetoxy-6/3-01. to cholestan-3/3- to dihydroxybutyric acid. usmg osmic acid/ acetoxy-6-one. 450 barium chlorate. 670 Cholestan-3/3-acetoxy-5a-ol-6-one. from cholestan- oxidation of. 640 3/3-acetoxy-5a .6/3-diol. 451 Crotyl alcohol. to crotonaldehyde. 832 Cholestan-3/3-acetoxy-6-one, from cholestan-3/3- Cryptopleurine. from julandine. 699 acetoxy-6/3-01. 450 Cyanoanils. from aminonitriles. 217 Cholestan-3/3-01. oxidation of by triphenyl bismuth• 4-Cyanocatechol. oxidation of. 383 carbonate. 827 a-Cyanoglyoxylidenedi-o-toluidine. preparation of. Cholestan-3-one. to 2.2-diphenylcholestan-3-one. 238 828 Cyanohydrins. oxidative cleavage of. using 5-a-Cholestan-3-one. from 5-a-cholestane-3-one Ag 2Co,,556 oxime. 834 Cyclic ether 5-a-Cholestane-3-one oxime. to 5-a-cholestan-3- from alicyclic alcohols. 769 one, 834 from cycloalkyl alcohols. 769 Cholestanol. to cholestanone. 830 from polycyclic alcohols. 769 Cholestanone. from cholestanol. 830 Cyclic ketones. to ring contracted acids. 849 INDEX 891

Cycloalkanes. oxidation of cis-Cyclohexane-I.2-diol. from cyclohexene. using C. 336 to adipaldehyde. 384 using chromyl acetate. 50 from cyclohexene. using OsO)N-methyl morpho• by RuO •. 463 line. 676 Cycloalkenes. oxidation of. using chromyl chloride. 10 hexane-I .6-dial. 820 64 trans-Cyclohexane-1.2-diol. to hexane-I.6-dial. 820 Cyc10alkyl alcohol. oxidation of. 769 Cyclohexane-1.2-dione bishydrazone. 10 cyclo• Cyclobutane. from I-hydroxymethylcyclobutan-I- hexyn. 395 01,780 Cyclohexanecarboxamide. to N-cyclohexylace• Cyclobutanecarboxylic acid tamide. 806 to cyclobutene. 793 Cyclohexanecarboxylic acid to cyc10butyl chloride. 794 10 cyclohexane. 793 Cyc1obutanol to cyc10hexyl chloride. 794 to or-hydroxy aldehydes. 19 1.2-Cyclohexanediol to 4-hydroxybutanol. 30 to 1.2-cyclohexanedione. 450 to ketones. 19 10 2-hydroxycyclohexanone. 450 Cyc1obutanols 1.2-Cyclohexanedione. from 1.2-cyc1ohexanediol. to a-(acylmethyl)-a./3-enones. 578 450 to cyc1obutanones. 450 1,2.3-Cyclohexanetriol. to pentanedial. 780 Cyclobutanone. from 1.1' -dihydroxydicyclobutyl. Cyclohexanol 780 to cyclohexanone. 465 Cyc1obutanones. from cyclobutanols. 450 from cyclohexene. 851 Cyclobulene. trom cyclobutanecarboxylic acid. dehydrogenatIon of. 577 793 Cyc1ohexanone oxime Cyclobulyl chloride. from cyclobutanecarboxylic to cyclohexanone. 734 acid. 794 from cyclohexylamine. 26 3a-5a-Cyclocholeslan-6/3-yl ethyl ether. oxidalion to gem-nitrosoacetoxycyclohexane. 806 of, 453 Cyclohexanone 3a-5a-Cyclocholeslan-6/3-yl melhyl elher. oxidation to a-acetoxycyclohexanone. 786 of, 453 10 2-acetoxycyclohexanone. 805 Cyc1ododecene 8aeyer-Villiger oxidation of. 849 10 a-chlorocyclodocedanone. 10 1 to bicyclohexyl-2,2'-dione. 385 to l.12-dodecanedioic acid. 18 from cyclohexane. 466 Cycloheplane from cyclohexanol. 465 10 cyc1oheptanone. 466 from cyclohexanone oxime. 734 10 pimelic acid. 466 to dodecane-I , 12 -dioale, 865 Cycloheptanone 2-Cyclohexen-I-ol. epoxidation of. 18 10 a-acelOxycycioheptanone. 788 Cyc10hexene from cycloheptane. 466 10 3-acetoxycyc1ohexene. 747 2.4 .6-Cydoheptatriene-l-carboxaldehyde dimethyl .to cis-2-(\ -adamanty lamino )cyclohexanol. 682 acetal. from cyclooctatetraene. 752 to adipaldehyde. 458 Cycloheptene. oxidative carbonylalion of. 499 using OsO./sodium periodate. 677 I-Cycloheptene-5-carboxylic acid. 104-cyclohep• to benzene. 477 lenyl acelate. 793 to cis-2-(tert-butylaminolcyclohexanol. 682 4-Cycloheptenyl acetate. from l-cycloheptene-5- to cyclohexane. 477 carboxylic acid. 793 from cyclohexanecarboxylic acid. 793 Cyclohexa-I.3-diene to cis-cyc1ohexane-1.2-diol. using OsO}N- 10 1,2-diacetoxycyclohexenes. 750 methyl morpholine. 676 10 IA-diacelOxycyciohexenes. 750 from cyclohexane-1.2-dione bishydrazone. 395 cis-I.3-Cyclohexadiene. 10 cis.cis-2.4-hexadicne• to cyclohexanol. 851 dial. 780 to cyc10hexene epoxide. 17 Cyclohexadienonyl phenyl elhers. preparalion of. 10 2-cyclohexene-I-ol. 360 187 to 2-cyclohexene-I-one. 360 Cyclohcxane to cyclohexeneoxide. 851 10 adipic acid. 466 to cyclohexenone. 157 10 cyclohexanone. 466 to cylcopentanecarboxaldehyde dimethyl acetal. from cyclohexene. 477 f710 Cyclohexane carboxylic acid. from phenylcyclo• to cis-I.2-diacetoxycyclohexane. 747 hexane. 465 to trans-I.2-diacetoxycyclohexane. 747 892 INDEX

Cyc10hexene (conI.) I A-Di-( I '-I' -2' -carboranyl)butadiyne. from ethy• to rrans-I.12-dichlorocyc1ohexane. 18 nylcarborane. 432 to cis-a.i3-epoxy alcohol. 17 a.a' -Diacetoxyacetone. from acetone. 786 to 1.6-hexanedioic acid. 18 cis-1.2-Diacetoxycyclohexane. from cyclohexene. oxidation of. by Mn(OAc),. 304 747 oxidation of. using OS041H202' 659 rrans-1.2 -Diacetox ycyclohexane. from cyclohexene. Cyc10hexene epoxide. from cyclohexene. 17 747 2-Cyclohexene-l-ol. from cyclohexene. 360 1.2-Diacetoxycyclohexenes. from cyclohexa-I.3- Cyclohexene-3-01. oxidation of. 851 diene. 750 2-Cyclohexene-I-one. from cyclohexene. 360 I A-Diacetoxycyclohexenes. from cyclohexa-I.3- Cyclohexeneoxide. from cyclohexene. 851 diene.750 Cyclohexenes. epoxidation of. 851 cis-9.IO-Diacetoxy-9.IO-dihydroanthracene. from Cyclohexenes(4-substituted 2-). fonnation of. 593 anthracene. using LTA. 755 Cyclohexenone. from cyclohexene. 157 trans-9.IO-Diacetoxy-9. IO-dihydroanthracene. from 2-(3-Cyclohexeny I)propanal. from 2-(3-cyc1ohex- anthracene. using LT A. 755 enyl)-I-propanol.561 2.7-Diacetoxynorbomene. from norbomadiene. 752 2-(3-Cyclohexenyl)-l-propanol. to 2-(3-cyclohex• Diacetoxynonricyclane. from norbomadiene. 752 enyl)propanal. 561 3i3-Diacetoxy-5a-pregnane-II.20-dione. from 313- Cyclohexyl chloride. from cyclohexanecarboxylic acetoxy-5a-pregnane-II.12-dione. 780 acid. 794 3i3.17/3-Diacetoxy-5.IO-seco-estrane-5.IO-dione. N-Cyclohexylacetamide. from cyclohexanecarbox• from estrane-3i3.5a. lOa. 17i3-tetrol-3. 17- amide. 806 diacetate. 780 Cyclohexylamine. to cyclohexanone oxime. 26 Diacyl hydrazides. from dicarbonyl azo compounds. cis-Cyclonon-3-ene-I.6-dione. from ci.l-1.6-dihy• 409 droxybicyclo[4.3.0J-non-3-enc. 780 1.4-Dialdehyde. from isobutyraldehyde. 385 Cyclooctatetraene 4 ,4-Dialkoxycyclohexa-2 .5-dienones. from phenols. to bicyclo[4.2.0jota-2A-diene-7.8-diol. 752 735 to 2A.6-cycloheptatriene-l-carboxaldehyde Dialkyl acetylenes dimethyl acetal. 752 to acyloins. 720 Cyclooctene. to 1.8-octanedioic acid. 18 to benzils. 753 Cyclopentanecarboxaldehyde dimethy I acetal. from Nb .Nb-Dialkyl-2' -3' .5' -tri-O-acyladonosines. oxida- cyclohexene. 710 tion of by RuO•• 454 Cyclopentanol. dehydrogenation of. 577 Dialkylaminoarenes. reaction with Ce(lV). 612 Cyclopentanone. to a-acetoxycyclopentanone. 786 2.6-Dialkylphenols. oxidation of. 735 Cyclopentanone 2A-dinitrophenylhydrazone. to 1- Diaryl acetylenes. to benzils. 720 (2 A-dinitropheny lazo )-I-acetoxycyclopen• 2.6-Diary 1-3.7-dioxabicyclo[ 3.3. Ojoctane-4. 8- tane. 801 diones Cyclopentene. oxidation of by Mn(OAch. 304 from p-alkoxycinnamic acids. 706 Cyclopropane. from oxazolidine. 407 from cinnamic acids. 731 Cyclopropane alcohols. nonconjugated. oxidation 1.2-Diarylethanes. oxidative coupling of. using of. using Mn02' 142 TUIII). 699 Cyclopropylcarbinols. oxidation of. 577 l.I-Diarylethylenes. to deoxybenzoins. 712 Diarylmethanes. oxidation of. using Mn02' 201 rrans-Decahydronaphthalenc. to rrans-9-decahy• 1.3-Diaryl-1.3-propancdiones. to 3-oxo-2.3-diaryl- dronaphthol. 463 propanoates.714 rrans-9-Decahydronaphthol. from Irans-decahydro- Diaryl sulfides. to sulfoxides. 586 naphthalene. 463 Diazepines. dehydrogenation of. using Mn02' 193 Decanoic acid. from I-octene. 310 Diazo compounds. preparation of. using Mn02• 221 I-Decene. to ')I-n-octylbutyrolectone. 308 a-Diazo ketone. from benzil monohydrazone. 395 4-Decenoic acid. from I-octene. 309 4-Diazo 1.2.5.6-tetramethyltricyclo-[3.1.0.02.b1- Dehydrogenation. using Mn02' 189 hexan-3-one. synthesis of. 239 (± )-6a. 7-Dehydro-3-methoxy-N-acetylnoman• Dibenzofuran. from cyclization of diphenylether. tenine. from (± )-3-methoxy-N-acetylnoman• 499 tenine. 729 2.2' -Dibenzoquinone. from I A-dimethoxybenzene. Deoxybenzoins. from I.I-diarylethylenes. 712 616-617 3-Deoxy-d-mannose. to 2-deoxy-d-ribose. 780 IA-Dibenzoylbutane 2-Deoxy-d-ribose. from 3-deoxy-d-mannose. 780 from cis-I.2-diphenylcyclohexane-I.2-diol. 780 1.2-Di-ladamantyl-( I )Jethane-I.2-diol.tol-fonnyl- from rrans-I.2-diphenylcyclohexane-I.2-diol. adamantane. 780 780 INDEX 893

N.O-Dibenzoylhydroxylamine. from benzoyl• Dihydrofurans hydroxylamine. 394 from enoiizable ketones and olefins using 2.2'-Dibromo-4.4' ,5,5'-tetramethoxybiphenyl. from Mn(OAch. 284 4-bromoveratrole. 729 fonnation of. from olefins. ketones. and 3,5-Di-t-butyl-I,2-benzoquinone. from 3.5-di-l• Mn(OAch. 284 butycatechol. 354 4,5-Dihydro-1.2-oxazoles. dehydrogenation of. 3,5-Di-t-butylcatechol. to 3.5-di-l-butyl-I.2-benzo• using MnO~. 190 quinone. 354 1,3-Dihydroxyacetone. to methyl glycolate. 543 3,5-Di-t-butyl-I,2-dimethoxybenzene. to 3.5-di-t• 313.1713-Dihydroxyandrost-4-ene. to testosterone. butyl-o-benzoquinone. 616-617 507 3,3' -Di-t-butyl-5.5' -diphenyldiphenoquinone. from endo.endo-2.3-DihydroxybicycloI2.2.1 )heptane. to 2-t-butyl-6-phenylphenol. 433 difonnylcyclopentane. 780 3.5-Di-t-butyl-o-benzoquinone. from 3.5-di-r-butyl- cis-I.6-DihydroxybicycloI4.3.0)-non-3-ene. to cis• 1.2-dimethoxybenzene. 616-617 cyclonon-3-ene.I.6-dione. 780 2.5-Di-t-butylhydroquinone. to 2.5-di-t-butyl• Dihydroxybutyric acid. from crotonic acid. using benzoquinone. 616-617 osmic acid/barium chlorate. 670 2,6-Di-t-butyl-4-hydroxy-4-methylcyclohexa-2.5- 1.1' -Dihydroxydicyclobutyl. to cyclobutanone. dienone 780 from 2.6-butyl-p-cresol. 436 2.6-Dihydroxy-3.4-dimethylbenzamide. to 2- from 4-methyl-2.6-di-t-butylphenol. 430 hydroxy-4.5-dimethyl-3.6-dioxocyclohexa- 2.6-Di-t-butylphenol. oxidation of. 822 1.4-dienecarboxanide. 626 2.6-Di-lerl-butyl-4-methylphenol Dihydroxydiphenyls. to diphenoquinones. using oxidation of. 427 Ag2COJ .548 oxidative dealkylation of. 383 20.21-Dihydroxy-ll13 .18-epoxy-5a-pregnan-3-one 1.2-Dicarbomethoxy-I.2-dicyano-I.2-di-tolyleth• diacetate. to 3-oxo-II13.20.21-trihydroxy- ane. from Methyl-p-tolylcyanoacetate. 434 5a-pregnan-18-oic acid 1l.18-lactone 20.21· Dicarbonyl azo compounds. to diacyl hydrazides. diacetate. 452 409 9.IO-Dihydroxyoctadecanoic acid. to nonanal. 780 trans-1.12-Dichlorocyclohexane. from cyclohexene. thre0-4.5-Dihydroxyoctane. from octene. 676 18 N-cbz-3-4-Dihydroxyprolinamines. oxidation of. Dichlorophenylmethane. to tetraphenylethene. 363 638 cis-Dicyanostilbenes. from phenylacetonitrile. 407 trans-I.2-Dihydroxy-I.2.3.4-tetrahydronaphthalene. rrans-Dicyanostilbenes. from phenylacetonitrile. to o-(2-fonnylethyl) benzaldehyde. 820 407 p.p' -Dihydroxystilbenes. to stilbenequinones. using 2.2'-Di-I5.5'·dimethyl)benzoquinone. from 2.5- Ag2CO~. 548 dimethoxytoluene.616-617 1O.11-Dihydroxyundecanoic acid. from sodium 10- Dienes undecenoate. 642 to tetrols. 645 2.6-Diisopropyl-I.4-dimethoxybenzene. to 2.6- to unsaturated diols. 645 diisopropylbenzoquinone. 616-617 4.5: 11.I2-Diepoxy-4.5: 11.I2-tetrahydro- 2.6-Diisopropylbenzoquinone. from 2.6-diiso• benzol a Ipyrene. synthesis of. 657 propyl-1.4-dimethoxybenzene. 616-617 Diethyl acetoxymalonate. from diethyl malonate. 1.2:5.6-Di-O-isopropylidene-o-glucofuranose. to 786 1.2:5.6-di-O-isopropylidene-a-o-ribohexo• Diethyldisulfide. from ethyl mercaptan. 407 furanos-3-ulose. 451 Diethyl malonate. to diethyl acetoxymalonate. 786 1.2:5.6-Di-O-isopropylidene-a-o-glucofuranose Diethyltartarate. to ethyl glyoxylate. 780 from 1.2:5.6-di-O-isopropylidene-a-o-ribohexo• p-Diftuoromethylnitrobenzene. from p-nitrotoluene. furanos-3-ulose. 451 407 to 1.2:5.6-di-O-isopropylidine-a-o-ribohexofura• Difonnylcyclopentane. from endo-endo-2.3-dihy• nosulose. 465 droxybicycloI2.2.llheptane. 780 1.2:5.6-Di-O-isopropylidene-o-mannitol. to 2.3- Di-O-fonnyl-o-erithrose. from o-glucose. 780. isopropylidene-o-glyceraldehyde. 832 804 1.2:5.6-Di-O-isopropylidene-a-o-ribohexofuranos- 1.8-Difonnylnaphthalene.from 1.2-dihydroacenaph• 3-ulose. from 1.2.5.6-di-O-isopropylidene• thene.780 o-glucofuranose. 451 1.2-Dihydroacenaphthene-I.2-diol. to 1.8-difonnyl• 1.2:5.6-Di-O-isopropylidene-a-o-ribohexofuranosu• naphthalene. 780 lose. from 1.2:5.6-di-O-isopropylidine-a-o• 9.10-Dihydroanthracene. to 10.10' -dioxodian• glucofuranose.465 thranyI. 297 Di-o-tolyldisulfide. from o-thiocresol. 833 4.5-Dihydrobenzopyrene. oxidation of. 639 Di-p-tolyldisulfide. from p-thiocresol. 833 894 INDEX

Di-p-tolylphenyl hydrazine. from p-tolylphenyl- 2.5-Dimethoxy-p-xylene. to 2.5-dimethylbenzoqui• amine. 390 none. 616-617 1.2-Diketone bishydrazones. oxidation of. 395 Dimethyl bicyclo(2.2.2Joct-5-ene-l.exo-2-dicarbox• 1.2-Diketone bisphenylhydrazone. oxidation of. 395 ylatc( 1-). from l-carbomethoxy-2-endo• Diketones. from polyols. using Ag2CO~. 531-534 carbomethoxybicyclo(2. 2 .2]octane-5 .6· from secondary a-ketoalcohols. using Mn(OAc),. endodicarboxylic acid. 805 290 Dimethyl docosa-IO.12-diynoate. preparation of. a-Diketones 431 from alkynes. 460 Dimethyl ent-3a.13-dihydroxy-2-oxo-20-norgibber• from a-aminoketones. 212 rella-I( 10). 16-dienc-7 .19-dioate. synthesis a-Diketones. oxidation of. 850 of. 240 1.4-Diketones. from isopropeny1acetate and ketones 2.6-Dimethyl-I.4-benzoquinone. from 4-hydroxy- using Mn(OAch. 286 3.5-dimethylbenzylalcohol. 822 2.5-Dimethoxy acetophenones. oxidation of. using 2.5-Dimethyl-1.4-dimethoxybenzene. to 2.4-di• T1(N03)3. 725 methylbenzoquinone.616-617 3.3-Dimethoxy-1.2-diary1propan-1-ones. synthesis 3.3-Dimethyl-l-indanone. from 1.I-dimethylindan. of. 732 99 2.5-Dimethoxy-4-(2-acetaminopropy1)toluene. to 2- 3.7-Dimethyl-I-octanol. to 4-methyl-5-i-pentyl• methyl-5-(2-acetaminopropyl)benzoquinone. THF.769 616-617 2. 7-Dimethyl-3.5-octadiyne.2. 7-diol. from 2- 2.5-Dimethoxy-4-(2-( N-I-butoxycarbonylamino)pro• methyl-3-butyn-2-01. 432 pyl)to1uene. to 2-methyl-5-(2-( N-I-butoxy• Dimethyl-3-acetoxyoctan-2-01. from 2.6-dimethy• carbonylaminoJpropyl)benzoquinone. loct-2-ene. 824 616-617 2.5-Dimethyl-3-acetyl-5-phenyl-dihydrofuran. from 1.4-Dimethoxy-2-allyl-3-methylnaphtha1ene. to 2- a-methylstyrene. acetylacetone. and allyl-3-methyl-I.4-naphthoquinone. 616-617 Mn(OAc)" 311 1.4-Dimethoxybenzene I-Dimethylaminonaphthalene. self-coupling of. 584 to p-benzoquinone. 616-617 4.4-Dimethyl-3a-androstan-2-one. to 3a-acetoxy- to 2.2'-dibenzoquinone. 616-617 4.4-dimethyl-5a-androstan-2-one. 286 1.4-Dimethoxybenzenes. oxidation of. 588 N.N-Dimethylaniline. to N-methylacetamide using 2.5-Dimethoxy-4-(2-( N-I-butoxycarbonylamino)• Mn(OAch.291 propyl)toluene. to 2-methyl-5-(2-(N-I-bu- 9.10-Dimethylanthracene. to 9.10-bis(acetoxy• toxycarbonylamino )propyl)benzoquinone. methyl)anthracene. 757 616-617 2.5-Dimethyl-d-arabinose. from 3.6-dimethyl-d• 6.7-Dimethoxy-3.4-dihydrocoumarin. from 3-(3.4- glucose. 780 dimethoxyphenyl)-propionic acid. 730 5.6-Dimethylbenzimidazol-2-one. demethylative 1.4-Dimethoxy-2-geranyl-3-methylnaphthalene. to nitration of. 592 2-geranyl-3-methyl-1.4-naphthoquinone. 2.4-Dimethylbenzoquinone. from 2.5-dimethyl-I.4- 616-617 dimethoxybenzene.616-617 1.4-Dimethoxy-2-methylnaphthalene. to 2-methyl- 2.5-Dimethylbenzoquinone. from 2.5-dimethoxy-p• 1.4-naphthoquinone. 616-617 xylene. 616-617- 4.4-Dimethoxy-4-methoxycyclolohexa-2.5-di• 2.6-Dimethylbenzoquinone. from 2.5-dimethoxy-m• enones. from 4-methoxy phenols. 726 xylene. 616-617 1.4-Dimethoxynaphthalene. to 1.4-naphthoquinone. 2.5-Dimethyl-4-methylbenzyl alcohol. to 2-hydrox• 616-617 ymethyl-5-methylbenzoquinone. 616-617 2.5-Dimethoxy-4-(2-nitropropenyl)toluene. to 2- 2.3-Dimethylbutane-2.3-diol. to acetone. 820 methyl-5-(2-nitropropenyl )benzoquinone. N.N-Dimethyldodecylamine. to N.N-dimethyldode• 616-617 cylamine N-oxide. 31 3-(3.4-Dimethoxyphenyl)propionic. oxidation of. N.N-Dimethyldodecylamine N-oxide. from N.N• using T1(1II). 702 dimethyldodecylamine. 31 3-(3.4-Dimethoxyphenyl)-propionic acid. to 6.7- 3.6-Dimethyl-d-glucose. to dimethyl-d-arabinose. dimethoxy-3.4-dihydrocoumarin. 730 780 1.4-Dimethoxy-2-prenyl-3-methylnaphtha1ene. to 2- 2.5-Dimethylhexane·2.3-diol. to 3-methylbutanal. prenyl-3-methyl-I.4-naphthoquinone. 616- 780 617 2.6-Dimethylhydroquinone. oxidation of phenol. 2.5-Dimethoxytoluene. to 2.2'-di(5.5'-dimeth• 860 yl)benzoquinone.616-617 I.1-Dimethylindan. to 3.3-dimethyl-l-indanone. 99 2.5-Dimethoxy-m-xylene. to 2.6-dimethylbenzoqui• 2.6-Dimethyloct-2-ene. 2.6·dimethyl-3-acetoxy• none. 616-617 octan-2-01. 824 INDEX 895

2.6-Dimethylphenol 2.2-Diphenylcholestan-3-one. from cholestan-3-one. oxidation of. 834 828 to 3.3' .5.S'-tetramethyldiphenoquinone. 562 cis-l.2-Diphenylcyclohexane-1.2-diol. to 1,4-diben• 4.S-Dimethyl-o-phenylenediamine. oxidation of. zoylbutane. 780 429 trans-l.2-Diphenylcyclohexane-I.2-diol. to 104- i3.i3-Dimethylproponoic acid. to neopentylchloride. dibenzoylbutane. 780 794 Diphenyldiazomethane. from benzophenone hydra- S.S-Dimethyl-N-( p-toluenesulfonyllsulfenylimine. zone. 394. 834 to S.S-dimethyl-N-( p-toluenesulfonyl)sul• Diphenyldisulfide. from thiophenol. 833 foximine. 466 l.2-Diphenylethanol. to 2-phenylacetophenone. 864 S.S-Dimethyl-N-( p-toluenesulfonyl)sulfoximine. Diphenylether. cyclization of to dibenzofuran. 499 from S.S-dimethyl-N-( ptoluenesulfonyl )sul• Diphenylglycolic acid. to benzophenone. 820 fenylimine. 466 Diphenylketene. from benzil monohydrazone. 395 Dinitrile. from o-phenylenediamine. 385 Diphenylmethane 1-(2.4-Dinitrophenylazo )-I-acetoxycyclopentane. to benzhydryl acetate. 757 from cyclopentanone 2A-dinitrophenylhy• to benzophenone. 407 drazone. 801 Diphenylmethanol. to benzophenone. 105 Diols. oxidation of. using OsO•• 649 2.6-Diphenyl-3-methoxy-p-benzoquinone. from 2.6- Diols. a./3-unsaturated. oxidation of. using MnO~. diphenylphenol. 437 139 2.3-Diphenyl-3-methoxypropanoate. from chalcone a-Diols. oxidative cleavage of. 519 dimethyl acetal. 715 erylhro-Diols. to a-hydroxy ketones. 519 2.6-Diphenyl-4-methoxyphenol. oxidation of. 427 cis-4.S-Diols. from ~4-steroids. 646 Diphenyl-I.2A-oxadiazole. from benzaldehyde cis-Diols. from alkenes. 637 oxime. 562 1.2-Diols. cleavage of by sodium bismuthate. 820 9.10-Diphenylanthrene. from tetraphenylethene. 65 1.4-Diols. to lactones. 509 2.6-Diphenylphenol I.S-Diols. to lactones. 509 to 2.6-diphenyl-p-benzoquinone. 437 1.6-Diols. to lactones. 509 to 2.6-diphenyl-3-methoxy-p-benzoquinone. 437 Diosphenolene. from 2-hydroxypulegone. 826 2.6-Diphenylphenoxyl. from 4-methoxy-2.6-diphe• 10.10-Dioxodianthranyl. from 9.IO-dihydroanthra- nylphenol. 434 cene.297 E-I.2-Diphenylprop-l-ene. from E-I-phenylpro• 1.3-Dioxolanes. from glycol. 498 pene.483 3.6-Dioxopyridazine. from maleic hydrazide. 409 Z-I.2-Diphenylprop-I-ene. from E-I-phenylpro• Dipentene. synthesis of. 411 pene.483 Diphenoquinones meso-2.3-Diphenylsuccinonitrile. from phenylace• from dihydroxydiphenyls. using Ag~CO,. 548 tonitrile. 407 from phenols. 364 Diphenylsulfide using AgzCO,. 545 to diphenylsulfone. 457 using Mn(OAcl,. 292 from thiophenol. 407 from p-unsubstituted phenols. using Ag=CO,. Diphenylsulfone from diphenylsulfide. 408. 457 548 Diplodialidine 8(7). synthesis of. 476 Diphenyl sulfide Dipyrromethanes. to dipyrroketones. 592 to diphenyl sulfone. 408. 466 4A-Disubstituted cyclohexa-2.5-dienones. from 4- Diphenyl sulfone substituted phenols. 726 from diphenyl sulfide. 466 N.N'-Disubstituted hydrazines. to azo compounds. from diphenyl sulfoxide. 466 797 Diphenyl sulfoxide. to diphenyl sulfone. 466 2.6-Disubstituted p-benzoquinones. from 2.6-disub• Diphenylacetaldehyde. oxidative decarnonylation stituted phenols. 726 of. 429 2.6-Disubstituted phenols Diphenylacetonitrile to 3-alkoxy-2.6-disubstituted benzoquinones. oxidative coupling of. 428 430 to tetraphenylsuccinotrile. 434 to 2.6-disubstituted p-benzoquinones. 726 Diphenylacetylene oxidative coupling of. 427. 440 to benzil. 460. 64S. 686 Disulfide from benzil bishydrazone. 395 from mercaptans. 358 oxidation of. 685 from thiol. using V. 27 Diphenylamine. to tetraphenylhydrazine. 390 from thiols. 722. 827 2.6-Diphenyl-p-benzoquinone. from 2.6-diphenyl• to thiosulfinates. using V. 29 phenol. 437 to thiosulfonates. using V. 29 896 INDEX

Diterpenes. oxidation of. using Ag,CO,. 535-541 Ethyl glyoxylate. from diethyl glyoxylate. 780 1.3-Dithianes Ethyl 6-heptenoate. from suberic acid (mono ethyl degradation of. 587 ester). 793 dethioacetahzation of using Tl(NO,),. 724 Ethyl 3-hydroxycyclobutane carboxylate. to ethyl 3- Dithioacetais. cleavage of. 614 ketocyclobutane carboxylate. 450 1.3-Dithiolanes. degradation of. 587 Ethyl 3-ketocyclobutane carboxylate. from ethyl 3- 1.3-Dithiolanes. dethioacetaiization of using hydrollycyclobutane carboxylate. 450

Tl(N03h. 724 Ethyl mercaptan. to diethyldisulfide. 407 Dodecane-1.12-dioate. from cyclohexanone. 865 Ethyl tetrahydronicotinate. dimerization of. 586 1.12-Dodecanedioic acid. from cyclododecene. 18 I-Ethyl-2-benzosuberone. from I-propylidenetet- Durene. oxidation of by Mn(OAch. 299 ralin.732 Duroquinone. from 2.3.5.6-tetramethyl-IA-dime- Ethyl-et-cyanooctanoate. from ethylcyanoacetate. thoxybenzene.616-617 414 2-Ethyl-3.5-dimethylpyrazine. oxidation of. 53 N-Ethyl-3-ethylpiperidine. oxidation of. 456 Enol esters Ethyl-3-hydroxycyclobutanecarboxylate. to ethyl-3- to esters. 84 ketocyclobutanecarboxylate. 465 to lactones. 84 Ethyl-3-ketocyclobutanecarboxylate. from ethyl-3- oxidation of. using sodium chromate. 90 hydroxycyclobutanecarboxylate. 465 5et.8et-Epidioxy-5.8-dihydroergosteryl acetate. from 5-Ethyl-5-( i-methyl-3-carbollypropyl) barbituric ergosteryl acetate. 626 acid. from 5-ethyl-5-( l-methyl-4-pentenyl) 56.86-Epidioxy-5.8-dihydrolumisteryl acetate. from barbituric acid. 466 lumisteryl acetate. 626 5-Ethyl-5-C1 -methyl-4-pentenyl) barbituric acid. to cis-et.6-Epoxy alcohol. from cyclohexene. 17 5-ethyl-5-( l-methyl-3-carboxypropyl) barbi• 2 .3-Epoxy-2 .3-dihydro-1 A-naphthoquinone. 1- turic acid. 466 naphthol. 626 Ethyl-et-phenylacetoacetate. from ethyl acetoace• 2-Epoxygeraniol from geraniol. 851 tate. 828 2.3-Epoxygeranyl acetate. from E-geraniol. 866 2-Ethyl-tetrahydrofuran. from I-hexanol. 769 1.2-Epoxypropane. industrial oxidation of. 15 Ethylbenzene Ergosteryl acetate. to 5et.8et-epidioxy-5.8-dihy- to acetopenone. 855 droergosteryl acetate. 626 oxidation of by Mn(OAc),. 299 Erythro-9.10-dihydroxy-stearic acid. from potas• to et-phenylethyl acetate. 757 sium oleate. 642 Ethylene Ester. from enol esters. 84 to acetaldehyde. 471 Esters to acetaldehyde dialkylacetal. 475 from benzyl ethers. 83 to /3-chloroethylacetateA73 dimerization of. 860 to glycoldiacetate. 473 et.6-unsaturated. to carbonyl compounds. 476 to glycolmonoacetate. 473 Estrane-36 .5et.1 Oet .17 6-tetrol-3 .17 -diacetate. to ollidation of in acetic acid. 473 36. 176-diacetoxy-5. lO-seco-estrane-5. 10- oxidation of in alcohols. 474 dione.780 ollidation of in water. 471 Estrone. to 3-( l-oxo-8B-methyl-5B-carboxY-lrans- to vinylacetate. 473 perhydroindanyl-4et-)propanoic acid. 465 p-Ethyltoluene. ollidation of by Mn(OAch. 297 Ethane-1.2-diol. to formaldehyde. 820 Ethynylcarborane. from IA di-( I' -I' -2' -carbora• Ethanol. to acetaldehyde usmg Ce(lV). 577 nyl)butadiyne. 432 Ethene I-Ethynylcyclohexanol. to I.I-butadiynilene-dicy• to i3-acetoxyacrylic acid. 494 clohexanol.431 10 acrylic acid. 494 3-Exo-chloro-2-exo-hydroxynorbomene. from Ethers norbomene.65 et-acetollylation of. 857 et-acyloxylation of. 854 dlmerization of. 860 Fatty acids. unsaturated. oxidation of. 459 oxidative cleavage of. using Ce(!V). 608 elldo-Fenchyl acetate. to 5-ollo-elldo-fenchyl Ethyl acetoacetate. to ethyl-et-phenylacetoacetate. acetate. 96 828 Ferricenium cations. from ferrocenes. 596 Ethyl N-acetyl-2-amino-7-(trimethylsilyl)-4.6-hepta• Ferrocenes diynoate. 432 bridged. oxidation of. using MnO,. 202 Ethyl cyclopentanecarboxylate. from I-pyrrohdino• to ferricenium cations. 596 I-cyclohexene. 802 Flavone. acetate. hydroxylation of. 659 INDEX 897

Flavones. fonnation of with PdCI,. 479 2-Geranyl-3-methyl-I.4-naphthoquinone. from 1.4- Fluorene dimethoxy-2-geranyl-3-methylnaphthalene. to fluorenone. 98. 297 616-617 Fluorenone Gibberellic acid. oxidation of. using MnO,. 236 from fluorene. 98. 297 Gibberellins. oxidation of. using MnO,. 137 p-Fluoromethylnitrobenzene. from p-nitrotoluene. Glucose phenylosotriazole. to 2-phenyl-1.2.3-tri- 407 azole-4-carboxylic acid. 578 Formaldehyde o-Glucose from cinnamic acid. 293 to di-O-formyl-D-erithrose. 804 from ethane-1.2-diol. 820 to di-o-fonnyl-d-erithrose. 780 from glycol. 780 L-Glycerinaldehyde Fonnamides. from tertiary amines. 212 from L-arabinose. 780 I-Fonnyl-5-(hydroxymethyl)cyclooctene. from 1.5- from d- fructose. 780 bis-(hydroxymethyl)cyclooctene. 141 from I-sorbose. 780 I-Fonnyladamantane. from 1.2-di-[adamantyl(l)] Glycerol. from allylalcohol. 642 ethane-1.2-diol. 780 Glycol o-Fonnylaminoacetophenone. from 3-methylindole. to 1.3-dioxolanes. 498 437 to formaldehyde. 780 o-Formylaminoacetophenone derivatives. from Glycoldiacetate. from ethylene. 473 indoles.430 Glycolmonoacetate. from ethylene. 473 2-Formylchromone. from 2-ihydroxy• Glycols. oxidations of. 383 methyl)chromone. 236 1.2-Glycols. C-C-scission of. 849 o-(2-Fonnylethyl)benzaldehyde. from rrans-I.2- Glyoxal. from a-methyl-d-glucoside. 780 dihydroxy-I.2.3,4-tetrahydronaphthalene. Glyoxal bisphenylhydrazone. to bisphenylhydra- 820 lone. 396 2-Formylphenylacetaldehyde. from indane-I.2-diol. Grisen-3-ones. to 3-alkylidene grisens. 458 804 Guanidino compounds. degradation of. using 2-Formyltetrahydropyran. from 2-hydroxymethyl• Ag 2CO).559 tetrahydropyran. 776 L-Gulono--y-Iactone. to L-ascorbic acid. 849 o-Fructose. to d-glycerinaldehyde. 780 Fuchsones 3.5-disubstituted. preparation of. 184. 185 from 4-hydroxytriphenylmethane. 383 Halcon process. 850 Fumaric acid Haloalkanes. Mn(OAc), initiated addition to unsatu• oxidation of. 850 rated systems. 286 using OsO •. 653 Halohydrins. rearrangements. using Ag,CO,. 558- Furan. to bifuryl. 489 559 (E)-9-(Furan-3' -yl)-2.6-dimethy Inona-2 .6-dien-4- Heck reaction. 482 one. from 4-hydroxydendrolasin. 561 Heptaldehyde Furfural. from furfuryl alcohols. 379 to heptanoic acid. 452 Furil. from furoin. 826 from I-octene. 458 a-Furoic acid. from a-furfuryl alcohols. 378 Heptanal. from I-heptanol. 102 Furoin. to furil. 826 n-Heptane. to isomeric n-heptyl trifluoroacetates. 742 Heptanoic acid. from heptaldehyde. 452 n-Heptanoic acid. to I-hexene. 793 Galacticol. to isogalactose. 848 I-Heptanol. to heptanal. 102 Geranial n-Heptylamine. to n-hexyl cyanide. 805 from geraniol. 105. 149. 832 Heteroaromatic bases to methylgcranate. 149 acylation of. 860 Geraniol alkylation of. 860 catalyzed mddation of. 15 Heterocyclic compounds. oxidative dimerization of. to citral. 379 using MnO,. 228 to 2-epoxygeraniol. 851 Hexachloroethane. from chlorofonn. 410 to geranial. 105. 149. 832 cis.cis-2,4-Hexadienedial. from cis-I.3-cyclohexa• to methylgeranate. 149 diene.780 E-Geraniol Hexane-I.6-dial epoxidation of. 29 from cis-cyclohexane-I.2-diol. 820 to 2.3-epoxygeranyl acetate. 866 from rrans-cyclohexanc-I.2-diol. 820 898 INDEX

1.6-Hexanedioic acid. from cyclohexene. 18 Hydroquinones (COni.) 2.5-Hexanedione. from acetone. 306 oxidation of. 427. 735 n-Hexanoic acid. to n-amyl iodide. 794 using Ag2CO,. 545 I-Hexanol. to 2-ethyl-THF. 769 Hydroxy acids 2-Hexanone. from I-hexene. 498. 853 to keto acids. 452 9.27 -Hexatriacontadiene-18-19-diol. from 9-octa• oxidation of decanal. 780 using OsO•• 651 I-Hexene a-Hydroxy acids to 2-hexanone. 498. 853 to a-keto acids. 166 from n-heptanoic acid. 793 oxidation of. 383 oxidation of with PdCI2• 477 Hydroxylactones. oxidation of. 451 n-Hexyl cyanide. from n-heptylamine. 805 -y-Hydroxy aldehydes. from cyclobutanol. 19 N-Hexylheptamide. oxidation of by RuO •• 453 Hydroxylamines Homoallyl trimethylsilyl ethers. epoxidation of. 17 aromatic. oxidation of. 392 Homoallylic alcohols. epoxidation of. 16 to C-nitroso compounds. using Ag2CO,. 553 Homo-terpenyl-methylketone. from d.l-a-terpineol. oxidation of. 394 301 using Mn02. 214 Hydrazides. oxidation of. using Mn02' 218 from secondary amines. 858 Hydrazine. tetrasubstituted. from secondary amines. 2-Hydroxyandrosta-IA-diene-3.17-dione. from 2a• 390 hydroxyandrosta-4-ene-3.17-dione. 826 Hydrazines 2a-Hydroxyandrosta-4-ene-3.17-dione. to 2-hy• to azo compounds. using Ag2CO,. 553 droxyandrosta-1.4-diene-3.17-dione. 826 oxidation of. using Mn02' 218 3-Hydroxyanthranilic acid. oxidation of. using 2-Hydrazinobenzothiazole. oxidation of. 392 Mn02.239 Hydrazobenzene. to azobenzene. 834 4-Hydroxybenzylalcohol. to lA-benzoquinone. 822 Hydrazones 4-Hydroxybutanol. from cyclobutanol. 30 monosubstituted. to N-acetyl-N' -acylhydrazones. Hydroxycarbamates. vicinal. from oletins. 644 800 2-Hydroxychalcones. to Irans-aurones. 292 oxidation of. 400-404 3-Hydroxychromane. from allyl phenyl ether. 713 using Ag2CO" 553 6-Hydroxychromans. to p-quinones. 588 using Mn02• 220 14-Hydroxycodeinone. from codeine. 157 Hydrindacenes. oxidation of. using chromium Hydroxy compounds. oxidation of. 387 trioxide. 57 5-Hydroxycoumarans. to p-quinones. 588 4-Hydrobenzaldehydes. from 4-hydroxymethylben• 2-Hydroxycyclohexanone. from 1.2-cyclohexane- zenes.338 diol.450 Hydrobenzoin 4-Hydroxydendrolasin. to (E)-9-(furan-3' -yl)-2.6- to benzaldehyde. 820 dimethylnona-2.6-dien-4-one. 561 oxidation of using Mn(OAc),. 290 5a-Hydroxy-313.1713-diacetoxyandrostane. oxidation meso-Hydrobenzoin. to benzaldehyde. 832 of. 578 Hydrocarbons. oxidation of. using Mn02' 198 19-Hydroxy-313.1713-diacetoxy-5-androstene. 577 4-Hydroperoxy-2.4-dimethylcyclohexa-2.5-dione. 4-Hydroxy-3.5-dimethylbenzylalcohol. to 2.6- from 2.4-xylenol. 626 dimethyl-lA-benzoquinone. 822 4-Hydroperoxy-4-methylcyclohexa-2.5-dione. from 2-Hydroxy-4.5-dimethyl-3.6-dioxocyc1ohexa-I.4- p-cresol. 626 dienecarboxanide. from 2.6-dihydroxy-3.4- 4-Hydroperoxy-4-methyl-2.6-di-l-butylcyclohexa- dimethylbenzamide. 626 2.5-dienone. from 4-methyl-2.6-di-l-butyl• 3-Hydroxytlavone. to o-benzoylbenzoic acid. 437 phenol. 602. 626 3-Hydroxytlavones. to depsides. 430 4-Hydroperoxy-2A.6-trimethylcyclohexa-2.5-dione. a-Hydroxyketones. from erythro diols. 519 from mesitol. 626 Hydroxylated benzoquinones. from hydroquinone. Hydroquinone 427 to lA-benzoquinone. 14 a-Hydroxymalonic acids. degradation of. 611 to p-benzoquinone. 616-617. 725 DL-4-Hydroxy-3-methoxymandelic acid. oxidation oxidation of. 588 of. 166 Hydroquinone. I-butyl. to I-butyl-p-benzoquinone. 4-Hydroxymelhylbenzenes. to 4-hydrobenzalde• 427 hydes. 338 Hydroquinones 2-Hydroxymethyl-5a-cholestan-2-01. to 2-choles• to 1.4-benzoquinones. 364 tanone.780 to p-benzoquinones. 543 2-(Hydroxymethyl)chromone. to 2-formylchro• to quinones. 20 mone.236 INDEX 899

I-Hydroxymethylcyclobutan-I-ol. to cyclobutane. 2 .3-lsopropylidenc-D-glyceraldehyde. from 1.2.5.6- 780 di-O-isopropylidene-D-mannitol. 832 2-Hydroxymethyl-5-methylbenzoquinone. from 2.5- 2' .3' -O-lsopropylidene-5' -oxo-6.5' -cyclouridine. dimethyl-4-methylbenzyl alcohol. 616-617 preparation of. 173 2-Hydroxymethyhetrahydropyran. to 2-fonnyltetra- hydropyran. 776 6-Hydroxymythyluracil. to orotic acid. 378 lulandine. to cryptopleurine. 699 5-Hydroxymethyluracil. oxidation of. 848 5-Hydroxy-l,4-naphthoquinone. from 1.5-naphtha- lenediol. 626 Keto acids. from hydroxy acids. 452 5-Hydroxy-6-oxo-7.8-epoxycholestane. from 5.7- a-Keto acids cholestadiene. 460 from a-hydroxy acids. 166 1.3-Bis-(hydroxyphenYl)propane. oxidative coupling oxidation of. 850 of. 21 a-Keto alcohols. secondary. oxidation to diketones 17a-Hydroxypregnan-20-one. from pregnan- using Mn(OAc),. 290 17a.20a-diol. 519 /3-Keto-aldehydes. from p--y-unsaturated ketones. la-Hydroxyprevitamin 0,. to l-ketoprevitamin 0,. 687 166 a-Keto amides. from a-keto imines. 356 2-Hydroxypulegone. to diosphenolene. 826 a-Keto imines. to p-keto amides. 356 Hydroxy-l.3-seco-2-nor-5a-androstane-I.3-dioic Ketols. from polyols. using Ag 2CO,. 531-534 acid. from 17/3-acetoxy-3-oxo-5a-androst-l• a-Ketols. oxidation of. 850 ene.466 Ketones monohydrazones. oxidation of. 394 4-Hydroxytriphenylmethane. to fuchsones. 383 Ketones la-Hydroxyvitamin D,. ollidation of. 166 a-acyloxylation of. 855 from alcohols using 2.2-bipyridinium chlorochromate. 78 Imidazolidinetriones. from indole-I.2-dicarboxa• using pyridinium chlorochromate. 77 mides.92 a-allenic. from I.l-disubstituted a-allenic alco- Imides. substituted. from substituted amides by hols. 379 RuO •. 453 from benzyl ethers. 83 Imines. to oxaziranes. 854 cyclic a./3-unsaturated. oxidation of. 459 Indane. to indanone. 620 from cyclobutanol. 19 Indane-l.2-diol. to 2-fonnylphenylacetaldehyde. dehydrogenation of. 861 804 dimerization of. 860 Indanone. from indane. 620 from a-olefins. 867 Indans. ollidation of. using chromium trioxide. 57 oxidation of. using OsO•. 649 Indole-I.2-dicarboxamides. to imidazolidinetriones. from secondary alcohols. 382 92 using Ag2CO,. 507. 520-523 Indoles using RuO •. 450 oxidation of. using MnO~. 228 by PdSO•. 497 oxidative cleavage of, 430 from semicarbazones. 722 oxidative coupling of. 490 la-Ketoprevitamin D,. from la-hydroxyprevitamin myo-Inosose phenyl hydrazone. oxidation of. 240 0,. 166 lodobenzene. coupling of with iodotoluene. 499 Ketoximes. a.i3-unsaturated. to isoxazoles. 479 4-(Iodophenyl)methanal. from 4-iodotoluene. 99 Kreysigine. synthesis of. 698 Iodotoluene. coupling of with iodobenzene. 499 4-Iodotoluene. to 4-(iodophenyl)methanal. 99 Isoboldine. from reticuline. 23 Lactams. from acylazocarboxylates. 224 Isobutyraldehyde Lactic acid. to acetaldehyde. 820 to 1.4-dialdehyde. 385 Lactols to 2-methyl-2-(2' -methyl-I' -propenoxy)propional• to lactones. 519 dehyde. 143 using Ag2CO,. 528-530 to tetramethylsuccinaldehyde. 143 Lactones Isocyanates. from unsubstituted amides. 797 from lA-diols. 509 Isoftavones. preparation of. 713 from 1.5-diols. 509 Iso galactose . from galacticol. 848 from 1.6-diols. 509 Isomeric n-heptyl triftuoroacetates. from n-heptane. from enol esters. 84 742 from lactols. 519 Isooxazoles. from a.P-unsaturated ketoximes. 479 using Ag2CO,. 528-530 900 INDEX

Lactones (cont.) (± )-3-Methoxy-N-acetylnomantenine (cont. ) from olefins. 233 from (± )-3-methylenedioxybenzyll-2-acetyl- from polyols. using Ag 2CO). 525-527 5.6.7-trimethoxy-l.2.3.4-tetrahydroisoqui•

a./3-unsaturated. fOmlation of. using Mn02 • 134 noline.729 Leuco malachite green. to malachite green. 584 4-Methoxybenzaldehyde. from 4-methoxybenzyl d-Limonene. oxidation of Mn(OAc),. 301 alcohol. 105 Linalool. synthesis of. 411 2-Methoxy-5-(2-benzaminopropyllbenzoquinone. Longifolene. reaction of. 749 from 2.4.5.-trimethoxy-l-(2-benzamino• Lumisteryl acetate. to 5/3.8/3-epidioxy-5.8-dihydro• propyl)benzene.616-617 lumisteryl acetate. 626 p-Methoxybenzhydryl acetate. from phenyl-p-me• 2.6-Lutidine. to 6-methyl-2-pyridinecarboxylic thoxyphenylmethane. 757 acid. 56 p-Methoxybenzyl acetate from p-methoxyphenylacetic acid. 793 from methoxytoluene. 757 Malachite green. from leuco malachite green. 584 4-Methoxybenzyl alcohol. to 4-methoxybenzalde• Maleic acid hyde. 105 oxidation of. using OsO•. 653 p-Methoxybenzylacetate. from p-methoxytoluene. to DL-tanaric acid. 851 294 Maleic acids. oxidation of. 850 p-Methoxybenzylaldehyde. from p-methoxytoluenc. Maleic hydrazide. to 3.6-dioxopyridazine. 409 294 Malonic acid. oxidation of. using 050•. 653 2-Methoxy-4-bromo-5-t-butylphenol. oxidation of. Mandelic acid 822 to benzaldehyde. 384. 820 4-Methoxy-2.6-diphenylphenol. to 2.6-diphenyl• to benzoic acid. 384 phenoxy I. 434 Manganese (Illl acetate D' -Methoxy-d-hydroxy-methyl-diglycolic aldehyde. anhydrous from a-Methyl-d-mannopyranoside. 780 preparation of. 263 I-Methoxynaphthalene. to I-methoxy-4-acetoxy• synthesis of. 307 naphthalene. 294 dihydrate 2-Methoxynaphthalene. to 2-methoxy-I.4-naphtho• preparation of. 266 quinone. 294 synthesis of. 308 2-Methoxy-I.4-naphthoquinone. from 2-methoxy• Manganese dioxide. preparation of. 121. 122 naphthalene. 294 D-Mannose. to d-arabinose. 780 4-Methoxy phenols. to 4.4-dimethoxy-4-methoxy• Matairesinol dimethyl ether. to cyc1ohexa-2.5-dienones. 726 (5aR.8aS.13a.13bR)2.3.11.12-tetramethoxy- 2-(4-Methoxyphenoxy)benzoic acid. oxidation of. 5.6.7 .8-tetrahydrobisbenzo\a.c )cyc1o• using TI(II). 730 octeno\6. 7-c )-2-tetrahydrofuranone. 729 p-Methoxyphenylacetic acid. to p-methoxybenzyl Mercaptans. to disulfides. 258 acetate. 793 Mesidine. oxidation of. 584 4-Methoxyphenylglyoxal bisbenzoy Ihydrazone. Mesitol. to 4-hydroperoxy-2.4.6-trimethylcyc1o• oxidation of. 397 hexa-2.5-dione. 626 6-Methoxytetralin. to l-acetoxy-6-methoxytetralin. Mesitylene 757.802 to bimesityl. 593 p-Methoxytoluene oxidation of by Mn(OAch. 299 to anisaldehyde. 296 Methacrolein. to methacrylic acid. 865 to p-methoxybenzyl acetate. 294. 757 Methacrylic acid. from methacrolein. 865 to p-methoxybenzaldehyde. 297 Methanal. from methanol. 18 oxidation of to substituted biaryls. 295 d.l-p-Methane-l.2.8-triol-l.2-diacetic. from d.l-a- N-Methylacetamide. from N.N-dimethylaniline terpineol. 301 using Mn(OAc»). 291 Methanol. to methanal. 18 2-Methyl-5-(2-acetaminopropyl)benzoquinone. from Methine compounds. activated. oxidative coupling 2.5-dimethoxy-4-(2-acetaminopropyl)tol• of. 440 uene.616-617 I-Methoxy-4-acetoxynaphthalene. from I-methoxy• Methyl-a-alkylarylacetates. from alkyl aryl acety• naphthalene. 294 lenes.720 3-Methoxy-N-acetylnomantenine. synthesis of. 698 2-0-Methylarabinose. from 3-0-methyl-D-glucose. (± )-3-Methoxy-N-acetylnomantenine 542 to ( ± )-6a. 7 -dehydro-3-methoxy-N-acetylnoman• a-Methyl-l-arabinosepyranoside. to L' -methyloxy• tenine.729 diglycolic aldehyde. 780 INDEX 901

Methylbenzenes Methylgeranate ammoxidation of. using V. 14 from geranial. 149 oxidation of. using cobalt catalysts. 339 from geraniol. 149 p-Methylbenzyl acetate. from p-xylene. 757 Methylglyoxal bisphenylhydrazone. to 1.2-bisphen• Methyl 4.6-0-benzylidene-2-deoxy-a-o-lyxo-hexo• ylazopropylene. 396 pyranoside. to methyl 4.6-0-benzylidene-2- a-Methyl-d-glucoside. to glyoxal. 780 deoxy-a-D-lhreo-3-hexulopyranoside. 451 3-0-Methyl-o-glucose. to 2-0-methylar.tbinose. Methyl 4.6-0-benzylidene-2-deoxy-a-o-lhreo-hexu• 542 lopyranoside. from methyI4.6-0-benzyli• Methyl glycolate. from 1.3-dihydroxyacetone. 543 dene-2-deoxy-a-o-lyxo-hexopyranoside. 451 Methyl hederagenin, to methyl hederagonate. 831 Methyl-benzylketone. from acetone and benzene Methyl hederagonate. from methyl hederagenin. using Mn(OAch. 289. 311 831 Methylbenzylsulfide. to methylbenzylsulfone. 457 Methyl-heptylketone. from acetone. I-hexene. and Methylbenzylsulfone. from methylbenzylsulfide. Mn(OAch.310 457 Methyl-7-(2-hydroxy-5-oxo-l-pyroridinylheptan• E-Methyl-p-bromocinnamate. 486 oate, synthesis of. 687 3-Methylbutanal. from 2.5-dimethylhexane-2.3- 2-Methyl-2-hydroxypropionic acid. to acetone. 820 diol.780 3-Methylindole. to o-fonnylaminoacetophenone. 3-Methylbut-2-enal. from 3-methylbut-2-en-I-oI. 437 832 Methylketones. from a-olefins. 475 3-Methylbut-2-en-I-ol. to 3-methylbut-2-enal. 832 O-Methylkreysigine, synthesis of. 698 4-Methyl-2-( I-i-butenyl)-tetrahydrofuran. from a-Methyl-d-mannopyranoside. to d' -methoxy-d- citronellol. 769 hydroxy-methyl-diglycolic aldehyde. 780 2-Methyl-5-(2-( N-I-butoxycaroonylamino)propyl)• Methyl a-methoxyarylacetates. from acetophe• benzoquinone. from 2.5-dimethoxy-4-(2- nones. 717 (N-I-butoxycarbonylamino lpropyl)toluene. Methyl-2(2' -methyl-I' -propenoxy )-propionalde• 616-617 hyde, from isobutyraldehyde. 143 2-Methyl-3-butyn-2-01. to 2.7-dimethyl-3.5-octa- 2-Methylnaphthalene diyne. 2.7-diol. 432 to l-acetoxy-2-methylnaphthalene. 297 3-Methylcatechol. oxidation of. 429 to 2-naphthoic acid. 98 4-Methyicatechol. to monomethylmuconates. 429 2-Methyl-I.4-naphthoquinone. from 1.4-dimethoxy- Methyl cinnamate. to aryl malonaldehydic acid 2-methylnaphthalene.616-617 dimethyl acetals. 733 2-Methyl-5-(2-nitropropenyl)benzoquinone. from Methyl cinnamates. to methyl-a-dimethoxymethy• 2.5-dimethoxy-4-(2-nitropropenyl)toluene. larylacetates. 715 616-617 Methyl 2.3-diaryl-3-methoxypropanoates 3a-Methyl-A-nor-5a-cholestane-3a.5-diol. to 4.5- from chalcone ketals. 733 seco-cholestane-3.5-dione, 780 synthesis of. 733 2-Methylnorbomene. to 3-methyl-3-nonricyclyl 4-Methyl-2.6-di-t-butylphenol acetate. 748 to 2.6-di-,-butyl-4-hydroxy-4-methylcyclohexa- 3-Methyl-3-nonricyclyl acetate. from 2-methylnor• 2.5-dienone. 430 bomene.748 to 4-hydroperoxy-4-methyl-2.6-di-l-butyicy• 9-Methyl-5( 10)-octalin-I.6-dione-I.6-bisethylene clohexa-2.5-dienone. 602. 626 thioacetal. to 9-Methyl-5(10)-octalin-1.6- Methyl-a-dimethoxymethylarylacetates. from dione-I-ethylene tioacetal. 734 methyl cinnamates. 715 9-Methyl-S( lO)octalin-I.6-dione-l-ethylene thio• I-Methylene-4-,-butyicyclohexane. oxidation of. acetal. from 9-methyl-S( JO)-octalin-I.6-di• 747 one-l.6-bisethylene thioacetal. 734 1-(3' .4' -Methylenedioxybenzyl)-2-acetyl-5 .6. 7- N-Methyloxalylpiperidine. to N-methyloxalyl-2- trimethoxy-I.2.3.4-tetrahydroisoquinoline. piperidone. 466 to (± )-3-methoxy-N-acetylnomantenine. N-Methyloxalyl-2-piperidone. from N-methyloxalyl• 729 piperidine. 466 (+ )-(lS.4R)-2-Methylenenorbomane. to (+)- 3-Methyl-l-oxo-1 .4.4a.5.6. 7 ,8.8a.octahydronaph• (lS.5S)-bicyclo[3.2.1I)-2-octanone. 731 thalene. preparation of. 102 Methyl esters, from aldehydes. using Ag 2COJ • 545 4-Methylpent-2.3-diene-l-ol Methyl ethyl ketone. to l-acetoxy-2-butanone. 786 to 4-Methylpent-2.3-diene-I-01 aldehyde, 379 Methylethylketone, oxidation of by Mn(OAch. 306 to 4-Methylpent-2,3-diene-I-ol amide, 379 4-Methylestra-1 ,3.5( JO)-trienes. oxidation of. 592 3-Methylpentane-1.3.5-triol. to mevalonolactone. Methylferrocene, oxidation of Mn(OAch, 305 561 902 INDEX

4-Methyl-i-pentyl-tetrahydrofuran. from 3.7- Neolitsine. synthesis of. 698 dimethyl-I-octano!. 769 Neopentylchloride. from .8.iJ-dimethylproponoic p-Methylphenols. to stilbenequinones. using acid. 794 Ag~C03' 548 a-Nitrato ketones Methyl phenylacetate. from acetophenone. 715 from acetophenones using TI(NO,l,. 718 Methylphenylacetylene. to l-phenylpropane-I.2- preparation of. 733 dione.686 Nitriles ,),-Methy I-,),-pheny Ibutyrolactone. from a-methy 1- dimerization of. 860 styrene. 308 hydrolysis of. using MnO,. 226 6-Methyl-2-pyridinecarboxylic acid. from 2.6-luti• Nitroalkanes. oxidation of. using Ce(lV). 610 dine. 56 Nitroanilines. oxidation of. 385 Methylpyridines. ammoxidation of. using V,O,. 14 p-Nitrobenzaldehyde. from p-nitrobenzylalcohol. a-Methy Istyrene 832 to l-acetoxy-2-phenyl-2-propano!. 824 4-Nitrobenzaldehyde diacetate. from 4-nitrotoluene. to ,),-methyl-,),-phenylbutyrolactone. 308 99 2-Methyl-THF. from I-pentanol. 769 Nitrobenzene. from benzeneamine. 12 p-Methylthioanisole. oxidation of. 292 Nitrobenzenes. from ani lines. 859 2-Methylthiophene. to thiopene-2-carbocylic acid. p-Nitrobenzyl acetate. from nitrotoluene. 757 98 p-Nitrobenzyl alcoho!. to p-nitrobenzaldehyde. 832 Methyl-p-tolylcyanoacetate. to 1.2-dicarbomethoxy- m-Nitrobenzylidene-o-phenylenediamine. oxidation 1.2-dicyano-I.2-di-tolylethane. 434 of. using MnO,. 238 Methyltolylsulfide. to methyltolylsulfone. 457 o-(p-Nitrobenzy lideneamino lphenol Methyltolylsulfone. from methyltolylsulfide. 457 to 2-(p-nitrophenyl)benzoxazole. 399 Methyl-3.4.6-tri-O-benzoyl-a-D-arabino-hexapY!1l- oxidation of. using MnO,. 238 nosidulose. from methyl-3.4.6-tri-O• Nitrones. from. secondary amines. 858 benzoyl-a-D-glucopyranoside. 465 2-(p-Nitrophenyllbenzoxazole. from o-(p-nitroben• Methyl-3.4.6-tri-O-benzoyl-a-D-glucopyranoside. to zylidineaminolpheno!. 399 methyl-3.4.6-tri-O-benzoyl-a-D-arabino• C-Nitroso compounds. from hydroxylamines. using hexapyranosidulose. 465 Ag,CO,.554 L' -Methyoxydiglycolic aldehyde. from a-methyl-I• a-Nitroso-a-aceto)(yalkanes. from aliphatic keto)(• arabinosepyranoside. 780 imes.798 Mevalonolactone. from 3-methylpentane-1.3.5-triol. gem-Nitrosoaceto)(ycyclohexane. from cyclohexa• 561 none oxime. 806 Monomethy1muconates. from 4-methylcatechol. 429 a-Nitrosotoluene. from N-benzylhydro)(ylamine. cis.cis-Muconate. from catechol monomethylether. 392 436 p-Nitrotoluene cis.cis-Muconic acid. from catechol. 383 to p-nitrobenzyl acetate. 757 cis-Muconitriles. from aromatic 1.2-amines. 796 oxidation of. 407 cis.cis-Mucononitrile. from o-phenylenediamine. 4-Nitrotoluene. to 4-nitrobenzaldehyde diacetate. 99 429.436 Nitroxyl radicals. from amines. 858 Myrcene. synthesis of. 411 Nonana!. from 9.IO-dihydroxyoctadecanoic acid. Myristic acid. from 1-pentadecene. 466 780 2-Nonenal. from 9. 10. 12-trihydroxyoctadecanoic Naphthalene acid. 780 oxidation of. 14 Norbomadiene to phthalic anhydride. 15 to 7-benzoyloxynorbomadiene. 855 1.4-Naphthalenedio!. to 1.4-naphthaquionone. 616- to bisnor-S. 342 617 to 7-I-butoxynorbomadienc. 855 1.5-Naphthalenediol. to 5-hydroxy-I.4-naphthoqui• to 2.7-diacetoxynorbomene. 752 none. 626 to diacetoxynonricyclane. 752 2-Naphthoic acid. from 2-methylnaphthalene. 98 Norbomene I-Naphthol. to 2.3-epoxy-2.3-dihydro-I.4-naphtho- to 3-exo-chloro-2-exo-hydroxynorbomene. 65 quinone. 626 to 3-oxo-3-methylene-4.7-methanobenzofuran • .8-Naphthol. to l-phenyl-2-naphthol. 834 309 Naphthols. oxidation of. with MnO,. 182 Norbomeol. to norcamphor. 450 1.4-Naphthoquinone Norcamphor. from norbomeol. 450 fonnation of. 590 A-Nor-2-a-methoxycarbonyl-3-androstan-17.8-yl from 1.4-dimethoxynaphthalene. 616-617 acetate. from 17-acetoxytesterone. 733 from 1.4-naphthalenediol. 616-617 (+ )-19-Nonestosterone. synthesis of. 476 INDEX 903

Nucleic acid derivatives. oxidative fragmentation 3-0xabicyclo[3. 3 .OJoct-7 -en-8-carbaldehyde. from of. using MnO,. 229 cis-2-oxahydrindane. 780 Oxadiazole. from benzaldehyde benzoylhydrazone. Ocoteine. synthesis of. 698 396 9-0ctadecanal. from 9.27 -hexatriacontadiene-18. 19- cis-2-0xahydrindane-cis-5.6-diol. to 3-oxabicyclo- diol. 780 [3.3.0)oct-7-en-8-carbaldehyde.780 Octaethyloxophlorine. from zinc octaethylpor• Oxaziranes. from imines. 854 phyrin. 731 Oxazolidine. to cyclopropane. 407 Octanal Oxazolines. dehydrogenation of. 408 from octene. 107 Oxidative aromatization. using MnO,. 189. 195 preparation of. 106. \08 N-Oxides. from teniary amines. 858 Octane-4.5-dione. from butyroin. 826 Oximes 1.8-0ctanedioic acid. from cyclooctene. 18 hydrolysis of. 6 \0 2-0ctanol. to 2-octanone. 849 oxidation of. 400-404 2-0ctanone. from 2-octanol. 849 using Ag2C03• 554 l-Octene to carbonyl compounds. 601 to decanoic acid. 3 \0 using MnO,. 214 to 4-decenoic acid. 309 from primary amines. 858 to heptaldehyde by RuO •• 458 Oxiranes. from alkenes. using chromyl acetate. 60 Octene a-Oxoacids. oxidation of. 383 to threo-4.5-dihydroxyoctane. 676 a-Oxoalcohols. oxidation of. 383 to octanal. 107 4-0xo-5a-androstan-17/3-01 propionate. from 5a- "(-n-Octylbutyrolactone. from I-decene. 308 androstane-4/3 .17/3-diol 17 -propionate. 776 Oletinic unsaturated systems 6-0xo-5a-androstane-3/3.17/3-diol 3.17/3-01-diace• Mn(OAch initiated addition of aldehydes to. 276 tate. from 5a-androstane-3/3 .6/3-17/3-triol Mn(OAch initiated addition of ketones to. 280 3.17 -diacetate. 776 Oletins 3-0xo-2.3-diarylpropanoates. from 1.3-diaryl-I.3- in acetic acid. 477 propanediones. 714 in alcohols. 477 5-0xo-endo-fenchyl acetate. from endo-fenchyl to ally 1 alcohols. 85 I acetate. 96 arylation of by PdCl,. 480 (I'RS.2 'RS)-8-0xo-3-endo-( I' .2' -dihydroxy• to "(-butyrolactones by oxidative addition of heptyl)tricyclo-4.3.0.0-nonane. synthesis of. carboxylic acids. 266 687 using chromate-iodine. 62 3-( I-Oxo-8/3-methyl-5/3-carboxy-trans-perhydroin• C=C cleavage of. 853 danyl-4a-)propanoic acid. from estrone. 465 dihydroxylation of. 853 2-0xo-3-methylene-4. 7 -methanobenzofuran. from epoxidation of. 853 norbonene. 309 fluorinated. oxidative cleavage of. 459 I-Oxo-IH.3H-naphtho[I.8-cd)pyran. from I.8-bis• a-hydroxylation of. 854 (hydroxymethyl)naphthalene. 140 ketone. addition to. by Mn(OAch. 280 II-Oxo-5a-pregnane-3/3.20/3-diol 3.20-diacetate. oxidation of from 5a-pregnane-3/3.II/3.20/3-triol 3.20- oxidative addition of acetic acid to. 269 diacetate. 776 oxidative addition of cyanoacetic acid to. 310 3-0xo-11I3 .20.2 I -trihydroxy-5a-pregnan-18-oic oxidative carbonylation of. 493 acid il.18-lactone 20.21-diacetate. from using sodium bismuthate. 824 20.21-dihydroxY-11I3.18-epoxy-5a-pregnan- using Tl(N03h. 731 3-one diacetate. 452 to vicinal hydroxycarbamates. 644 3-0xobisnor-4-cholen-22-al. to progesterone. 429. in water. 475 435 a-Oletins II-Oxoheptadecyl iodide. from 12-oxostearic acid. to aldehydes. 475 794 to methylketones. 475. 867 2-0xohomoadamantan-3-one. from adamantan-2-01. cis-Oletins. dihydroxylation of. 867 601 Organoboranes. oxidation of. using pyridinium 23-0xosolacongestidine. from solacongestidine. 156 chlorochromates. 95 12-0xostearic acid. to Il-oxoheptadecyliodide. 794 Organometallics. ligand dissociation of. with Oxygen insenion reactions by RuO •• 457 Ce(IV). 621 Oxythallation reactions. 709 Orotic acid from 6-hydroxymythyluracil. 378 I-Pentadecene. 10 myristic acid. 466 from 2-thiouracil. 378 Pentan-I-ol. to pentanal. 830 904 INDEX

Pentanal. from pentan-I-ol, 830 o-Phenylenediamines. oxidative cleavage of. 441 Pentanedial. from 1,2,3-cyclohexanetriol. 780 2 -Pheny lethanol. to pheny Imethanal. 19 I-Pentanol. to 2-methyl-tetrahydrofuran. 709 Phenylethene. to l-phenyl-2-iodoethanone. 100 Peptide bond cleavage. using OS04. 658 a-Phenylethyl acetate. from ethylbenzene, 757 Phenanthrene Phenylethylamine. to lrans' -a-a' -stillbenedicarbo- to 9-acetoxyphenanthrene. 297 nitrile. 390 to 9, lO-phenantraquinone, 461 Phenylglyoxal bisbenzoylhydrazone. oxidation of. 9,IO-Phenanthraquinone. from phenanthrene. 461 397 Phenanthrenequinones. fonnation of. 591 Phenylglyoxal bisphenylhydrazone, to triazoles. Phenols 396 to 4-alkyl-4-alkoxycyclohexa-2.5-dienones. 735 Phenylhydrazine. oxidation of. 392 to benzoquinones. 364 Phenylhydrazones to p-benzoquinones. 725 oxidation of, 400-404 to 4,4-dialkoxycyclohexa-2.5-dienones. 735 using Mn02. 224 dimerization of. 860 Phenylhydrazotriphenylmethane. to phenylazotri• to diphenoquinones. 364 phenylmethane. 834 using Ag2C03• 545 Phenylhydroxylamine. to azoxybenzene. 392 using Mn(OAch. 292 Phenyl methanal oxidation of. 386 from 2-phenylethanol. 19 by sodium bismuthate. 820 from phenylmethanol. 70 oxidation of monohydroxylic by LTA. 782 Phenylmethanol. to phenyl methanal. 70 oxidative coupling of. using Mn02. 178 Phenylnitromethane. from benzene. nitromethane, oxidative polymerization of. using Mn02' 182 and Mn(OAch. 311 oxygenation to benzoquinones. 441 I-Phenyl-2-iodoethanone. from phenylethene. 100 phenylation of. 828 I-Phenyl-2-naphthol. from l3-naphthol. 834 to polyphenylene ethers. using Mn(OAc),. 292 Phenyl-4-methylthiosemicarbazide. oxidation of. p-unsubstituted. to diphenoquinones. using 408 Ag2C03.548 Phenyl-p-methoxyphenylmethane. to p-methoxy• Phenothiazines. oxidation of. 408 benzhydryl acetate. 757 Phenylacetate. from benzene, 499 2-Phenyl-propionaldehyde, oxidative decarbonyla• Phenylacetic acid tion of. 429 to benzylacetate. using Mn(OAch. 293 5-Phenyl-l-pentanol. from 2-benzyl-tetrahydro• to benzylchloride. 794 furan.769 Phenylacetonitrile. oxidation of. 407 I-Phenylpropane-I.2-dione. from methylphenylace• 2-Phenylacetophenone. from 1.2-diphenylethanol. tylene.686 864 3-Phenyl-l-propanol Phenylacetylene. to benzoic acid. 686 to chroman. 580 a Phenyl alcohols. Fenton oxidation of. 849 to 4-chromanone. 580 2-Phenylazo-2-acetoxybutane. from 2-butanone to chromone. 580 phenylhydrazone, 801 to 3-phenylpropionic acid. 378 2-Phenylazo-2-acetoxypropane. from acetone phen• 2-Phenylpropene. to l-acetoxy-2-phenylpropan-2- ylhydrazone. 801 01. 824 Phenylazotriphenylmethane. from phenylhydrazotri• E-I-Phenylpropene. to E-1.2-diphenylprop-I-ene. phenylmethane. 834 483 2-Phenylbenzothiazole. from 2-hydrazinobenzothia• Z-I-Phenylpropene. to Z-I.2-diphenylprop-I-ene. zole.392 483 4-Pheny Ibutan-I-ol. to 2-pheny ltetrahydrofuran. 3-Phenylpropionic acid. from. 3-phenyl-I-propanol. 864 378 a-Phenylcinnamic acids. to 2-acetoxy-I.2-diphenyl• 2-Phenylpyridine. from benzonitrile. 361 ethanones. 293 2-Phenyltetrahydrofuran. from 4-phenylbutan-I-ol. Phenylcyclohexane. to cyclohexane carboxylic acid. 864 465 2-Phenyl-I.2,3-triazole-4-carboxylic acid, from 1-Phenylcyclohexene glucose phenylosotriazole. 579 to cis-2-acetoxy-l-pheny lcyclohexanol. 824 Phleomycin A2• to bleomycin A2• 409 to 2-(len-butylamino-I-phenyl cyclohexanol. 682 Phosphorous compounds, oxidation of. using Phenylenediamine. oxidative cleavage of. 429 Mn02.231 0-Phenylenediamine Phthalic anhydride. from naphthalene. 15 to cis.cis-mucononitrile, 429. 436 Pimelic acid. from cycloheptane. 466 to dinitrile. 385 Pinacol. to acetone. 780 INDEX 905 a-Pinene Proteins. crosslinking of, using OsO". 658 to cis-2-acetoxy-pin-3-ene. 749 Pyrans. oxidation of. using 050•. 646 to trans-pinocarvyl acetate. 750 a-Pyrazines. from a-aminoketones. 212 to a-terpineol-acetate. 302 Pyrazoles. from chalcone phenylhydrazones. 395 trans-Pinocarvyl acetate. from a-pinene. 750 Pyrazolines_ dehydrogenalton of. 408 Piperil. from piperoin. 826 5-Pyrazolones. to 2-alkynoic esters. 734 Piperoin. to piperil. 826 3-substituted 5-Pyrazolones. to 2-alkynoic esters. Poly-2.6-dimethyl-l,4-phenylene ether. from 2.6- using TI(NO,h. 720 xylenol. 383 3,4-disubstituted 5-Pyrazolones. to allenic esters. Poly-2.6-disubstituted-l,4-phenylene ether. from using Tl(NO,h, 721 2.6-disubstituted phenols. 427 1-(2-Pyridyl)-4-methylthiosemicarbazide, to triazo• Polycyclic alcohols. oxidation of. 769 lopyridine. 408 Polycyclic arenes. to quinones. 618-619 Pyrroles. oxidative coupling of. 490 Polycyclic aromatic hydrocarbons. oxidation of. 14. I-Pyrrolidino-l-cyclohexene. to ethyl cyclopentane• 602 carboxylate. 802 Polyhydroxy compounds. oxidation of. using MnO~. 172 Polynuclear hydrocarbons. oxidation of. using Quinine. oxidation of. 834 Cr(VI). 59 Quinizarin. to 1.4.9, lO-anthradiquinone. 616-617 Polyols Quinolideperoxides. from 4-alkyl-2.6-di-butyl- phenols. 430 to diketones. using Ag 2C03• 531-534 to ketols. using Ag~C03. 531-534 Quinols. oxidation of. using Ce(IV). 616 to lactones, using Ag~C03' 524-527 o-Quinonemonoanil. from o-aminophenol. 545 oxidation of. using MnO~, 139 Quinones Polyphenylene ethers. from phenols using from hydroquinones. 20 Mn(OAch. 292 oxidation of. using OS04. 646 Polyphenylene oxide. from 2,6-xylenol by oxidative by oxidation of hydroquinones with MnO~. lSI polymerization. 821 from polycyclic arenes. 618-619 Porphyrins. oxidation of using Tl(IIl), 707 p-Quinones. from 5-hydroxycoumarans. 588 Potassium oleate. to erythro-9.IO-dihydroxystearic p-Quinones. from 6-hydroxychromans. 588 acid, 642 Pregnan-17a.20a-diol. to 17a-hydroxypregnan-20- Regio stereoselective epoxidation. 853 one. 519 Reticuline. to isoboldine. 23 Pregnan-17a.2013-diol. to androstan-17-one. 519 Retinal. from vitamin A. 379 5a-Pregnane-3.20-dione. from 5a-pregnane- Ring contracted acids. from cyclic ketones. 849 313 .2013-diol. 450 Ruthenium tetroxide. preparation of. 464 5a-Pregnane-313.llI3.2013-triol 3.20-diacetate. to 1I-oxo-5a-pregnane-313.2013-diol 3.20-diace• tate. 776 Schiff bases •.oxidation of. 406 5a-Pregnane-313 .2013-diol. to 5a-pregnane-3.20- 4.5-Seco-cholestane-3.5-dione. from 313-methyl-A- dione.450 nor-5a-cholestane-3a.5-diol. 780 2-Prenyl-3-methyl-l,4-naphthoquinone. from 1.4- Selenides. to selenoxides using Tl(NO,h. 723 dimethoxy-2-prenyl-3-methylnaphthalene. Selenoxides. from selenides using TI(NO,h, 723 616-617 Semicarbazones Progesterone. from 3-oxobisnor-4-cholen-22-al. to aldehydes. 722 429.435 to carbonyl compounds. 601 Propanal. from I-propanol. 18.776 hydrolysis of. 610 I-Propanol. to propanal. 18. 776 to ketones. 722 2-Propanol. to acetone. 776 Septicine. to tylophorine. 699 Propargyl alcohol. to propynal. 577 Sesquicarene. synthesis of. 152 Propene Silver carbonate. preparation of. 560 from butyric acid. 861 Sodium lO-undecenoate. to 1O.II-dihydroxyundeca- to iso-propenylacetate. 477 noic acid. 642 iso-Propenylacetate. from propene. 477 Solacongestidine. to 23-oxosolacongestidine. 156 Propiolic acid. from propargyl alcohol. 378 L-Sorbose. to I-glycerinaldehyde. 780 i-Propyl chloride. from i-butyric acid. 794 Steroids I-Propylidenetetralin. to l-ethyl-2-benzosuberone. oxidation of. using Ag 2CO,. 535-541 732 oxidative ring contraction. 188 Propynal. from propargyl alcohol. 577 unsaturated. oxidation of. 459 906 INDEX

t:. 4 -Steroids. to cis-4.5-diols. 646 9.3' ,9' .9 "-Tetracarbazole. from carbazole. 390 Stilbenequinones 7.7.8.8-Tetracyanoquinonedimethane. preparation from p.p'-dihydroxystilbenes. using Ag,CO,. 548 of. 191 from p-methylphenols. using Ag,CO,. 548 Tetracyclonc. to tetraphenyl-2-pyrone. 581 cis-Stilbenes. from aryldiazomethanes. 586 Tetrahydro-I.4-benzodiazepine. oxidation of. trans-Stilbenes. from aryldiazomethanes. 586 453 trans-a-a' -Stilbenedicarbonitrile. from phcnylethyl- .:. """O"-Tetrahydrocannabinyl acetates. oxidation of. amine, 390 593 Straus coupling. 426 Tetrahydrofuran Styrene, to acetophenone. 853 from I-butanol. 769 Styrenes. to arylacetaldehydes. 712 to butyrolactone. 452 2-Styrylindoles. from azirines. 356 from primary alkanols. 579 Suberic acid (mono ethy I ester). to ethy I 6-hepten• Tetrahydrofurans. from alcohols. using LTA. 80:! oate, 793 Tetralin 4-Substituted phenols. to 4.4-disubstituted to I-acetoxytetralin. 757 cyclohexa-2.5-dienones. 726 oxidation of. using chromic acid. 58 Succinic anhydride. from acetic anhydride. 306 to a-tetralone. 341 Succinimide. from butyrolactam. 453 to I-tetralone. 620 Sulfenylimines. to sulfoximines. 457 Tetraline. to tetralone. 855 Sulfide. to sulfoxides. using V. 28 Tetralins. to tetralones. 100 Sulfides Tetralone. from tetraline. 855 oxidation of. 614 C/-Tetralone using MnO,. 229 to 2-acetoxy-a-tetralone. 786 oxygenation of. 359 from tetralin. 341 to sulfoxides. 13. 602. 859 I-Tetralone. from tetralin. 620 using TI(N03h. 723 Tetralones Sulfones from olefins. ketones. and Mn(OAch. 285 from sulfides. 859 from tetralins. 100 from sulfoxides, 13 a-Tetralones. from addition of aromatic ketones to Sulfoxide, oxygenation of, 359 olefins. using Mn(OAch. 285 Sulfoxides (5aR.8aS.13a.13bR)2.3.11.12-Tetramethoxy- from diary I sulfides, 587 5.6,7 .8-tetrahydrobisbenzo[a.c )cyclooc• from sulfides, 13. 602, 859 teno[6.7-c]-2-tetrahydrofuranone. from ma• using TI(N03h, 723 tairesinol dimethyl ether. 729 using V, 28 2.3.4,5-Tetramethoxy-6-allyltoluene. to 2-allyl-3- to sulfones, 13 methyl-5.6-dimethoxybenzoquinone. 616- Sulfoximes, from sulfenylimines, 457 617 Sulfur compounds, oxidation of, 409 2.3.4.5-Tetramethoxy-6-geranyltoluene. to 2-allyl- 3-methyl-5.6-dimethoxybenzoquinone. 616- 617 DL-Tartaric acid. from maleic acid, 851 3,3.5.5-Tetramethylcyclohex-I-enyl benzoate. to Terpenes 3,3 .5-tetramethy 1-6-oxocyclohex-I-eny I to -y-butyrolactones by oxidative addition of benzoate. 107 acetic acid using Mn(OAch. 274 3.3' .5,5'-Tetramethyldiphenoquinone. from 2,6- oxidation of. using MnO,. 149 dimethylphenol. 562 a-Terpineol. synthesis of, 411 2.3.5.6-Tetramethyl-1.4-dimethoxybenzene. to d.l-a-Terpineol duroquinone.616-617 to homo-terpenyl-methylketone. 301 3,3.5-Tetramethyl-6-oxocyclohex-I-enyl benzoate. to d.l-p-methane-l.2.8-triol-1.2-diacetic. 301 from 3.3.3 .5-tetramethylcyclohex-1-enyl a-Terpineol-acetate. from terpineol. 302 benzoate. 107 Teniary amines. to amine oxides, 26 Tetramethylsuccinaldehyde. from isobutyraldehyde. Testosterone 143 to androst-4-ene-3-17-dione. 830 cis-1.1.4.4-Tetramethyltetraline-2.3-diol. to 1.2- from 3f3.17f3-dihydroxyandrost-4-ene. 507 bis{2-formyl-propyl(2)]benzene. 780 oxidation of by RuO •. 459 Tetrapheny lethene 2.3,5.6-Tetrabromobenzoquinone. from 2,3.5.6- from dichlorophenylmethane. 363 tetrabromohydroquinone. 616-617 to 9. IO-diphenylphenanthrene. 65 2.3.5.6-Tetrabromohydroquinone. to 2.3.5.6-tetra• Tetraphenylhydrazine. from diphenylamine. 390 bromobenzoquinone. 616-617 Tetraphenyl-2-pyrone. from tetracyclone. 581 INDEX 907

Tetraphenylsuccinonitrile. from diphenylacetoni• Triazoles (COni.) trile. 428. 434 from 1.2-diketone bisphenylhydrazone. 396 2.2'.6.6'-Tetrasubstituted biaryls. synthesis of. 697 to phenylglyoxal bisphenylhydrazone. 396 3,3.5.5-Tetrasubstituted diphenoquinones. from Triazolpyridines. from Denzil monohydrazone. 395 2.6-disubstituted phenols. 427 2.4.6-Tri-t-butylphenol Tetrols. from dienes. 645 to 2-acetoxy-2.4.6-tri-t-butylcyclohexa-3,5- Theophyllines. synthesis of. 405 dienone. 804 Thiazoles. dehydrogenation of. 408 to 4-acetoxy-2.4 .6-tri ·t-butylcyclohexa-2 ,5- Thiiran. to thiiran I-oxide. 33 dienone. !l0~ Thiiran I-oxide, from thiiran. 33 oxidation of, 823 Thioanisole. to acetoxymethylenephenylsulfide. 1.1.1-Trichloro-3-chloronane. from I-octene. using Mn(OAch. 292 carbon tetrachloride. and Mn(OAch. 311 o-Thiocresol. to di-o-tolyldisultide. 833 9,lO.12-Trihydroxyoctadecanoic acid. from 2- p-Thiocresol. to di-p-tolyldisulfide. 833 nonenal. 780 Thiol. to disulfide. using V. 27 3.4.5-Trimethoxybenzaldehyde. from 3.4 .S-trime• Thiols thoxybenzyl alcohol. 105 to disultides. 722. 827 2.4.5-Trimethoxy-I-(2-benzaminopropyl)benzene. oxidation of. using V, 12 to 2-methoxy-S-(2-benzaminopropyl)benzo• Thiopene-2-carbocylic acid. from 2-methylthio• quinone. 616-617 phene.98 3.4,5-Trimethoxybenzyl alcohol. to 3.4.5-trime• Thiophenol thoxybenzaldehyde. 105 to diphenyldisulfide. 833 3.4.S-Trimethoxycinnamic acid, to 2.6-bis(3.4.S• to diphenylsulfide. 407 trimethoxyphenyl)3.7-dioxabi• Thiosemicarbazides. oxidation of. 408 cyclo[3.3.010ctane-4.8.dione. 731 Thiosulfinates. from disultides. using V, 29 2.4.4-Trimethylpentanal. from 2.4.4-trimethyl-l• Thiosulfonates. from disulfides. using V. 29 pentene. 101 2-Thiouracil, to orotic acid. 378 1.3.5-Trimethyl-2.4-bis( l-methoxycarbonyl-2- Thioxanthene. to thioxanthone. 591 ethenyl)benzene. preparation of. 498 Thioxanthone. from thioxanthene, 591 2.4.4-Trimethylpent-I-ene. oxidation of. 640 D-Threose. from D-xylose. 542 2.4.4-Trimethyl-l-pentene. to 2.4.4-trimethylpen• Tigogenin. to tigogenone. 830 tanal.IOI Tigogenone. from tigogenin. 830 Triphenylacetic acid. to triphenylmethyl acetate. Tioethers. a-acetoxylation of. 857 793 Toluene Triphenylmethyl acetate. from triphenylacetic acid, to benzaldehyde. 855 793 to benzoic acid. 407 5.5.5-Triphenyl-l-pentanol. to 2.2.3-triphenyl• to benzyl acetate. 757 tetrahydrofuran. 769 to bitolyls. 499 2,2,3-Triphenyl-tetrahydrofuran. from 5,5.5- to cresol acetates. 499 triphenyl-l-l-pentanol, 769 I-(p-Toluidinomaphthalenesulfonic acids. dimeriza• Triterpenes. oxidation of. using Ag2CO~. 535-541 tion of, 585 Tylophorine, from septicine. 699 N-(p-Tolyl)-p-benzoquinone. from p-tolylphenyl- amine. 390 p-Tolylmercuric acetate. to cresol acetates. 499 Unsaturated alcohols. intramolecular cyclization of. p-Tolylphenylamine. oxidation of. 390 773 3a,7a, 12a-Triacetoxy-24,24-diphenyl-5/3-chol-23- Unsaturated aldehydes. from olefins and aldehydes ene using Mn(OAch, 310 to 3a.7a.12a-triacetoxy-24-nor-5/3-cholan-23-al. Unsaturated diols. from dienes. 645 466 /3,.y-Unsaturated ketones. to /3-keto-aldehydes. 687 to 3a,7a, 12a-triacetoxy-24-nor-5/3-cholan-23-oic Unsaturated systems. addition of aldehydes to with acid. 466 Mn(OAch. 276 3a.7a.12a- Triacetoxy-24-nor-5/3-cholan-23-al, Unsubstituted amides. to isocyanates. 797 from 3a.7a.12a-triacetoxy-24.24-diphenyl- 5/3-chol-23-ene. 466 3a. 7 a.12a-Triacetoxy-24-nor-5/3-cholan-23-oic i-Valerie acid. to i-butyl chloride. 794 acid. from triacetoxy-24,24-diphenyl-5/3- n-Valerie acid. to n-butyl chloride. 794 chol-23-ene, 466 Vinylacetate, from ethylene. 473 Triazoles (S)( + )-2-Vinyl-2.3-dihydrobenzofuran. preparation from bishydrazone. 396 of. 498 908 INDEX

Vitamin A. 10 relinal. 379 2.4-Xylenol. 104-hydroperoxy-2.4-dimethylcy• Vitamin A alcohol. 10 vitamin A aldehyde. 832 clohexa-2.5-dione. 626 Vitamin A aldehyde. from vitamin A alcohol. 2.6-Xylenol 832 to 2 -acetoxy-2 .6-dimethy lcyclohexa-3 .5-dienone. 821 oxidative polymerization of to polyphenylene Xanthanone. from xanlhene. 591 oxide. 821 Xanthene. to xanlhanone. 591 to poly-2,6-dimethyl-IA-phenylene ether. 383 m-Xylene. oxidation of by Mn(OAch. 299 2,3-,2,5-.3.5-Xylenols, oxidation of. 590 o-Xylene. oxidation of by Mn(OAch. 299 D-Xylose. to D-threose, 542 p-Xylene to benzoyloxy-p-xylene. 868 to p-methylbenzyl acetate. 757 Zinc octaethylporphyrin. to octaethyloxophlorine. oxidation of by Mn(OAch. 299 731