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Oxidations of Organic Compounds Leading to Specific Oxidation Products

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Oxidations of Organic Compounds Leading to Specific Oxidation Products 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 I ''''"''w"' ~ 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<J """ is ~ Q. 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.
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