3632 SUBJECT INDEX

1,3-dipole, 916, 917,1217, 1504, 1505 2-nitroaniline, 142, 1868 1,3-oxazine, 1913 2-nitrobenzaldehyde, 136 1,3,2-benzothiazathiolium chloride, 1395 2-nitropropane, 1336, 1337 1,3,5-trihydroxybenzene, 1498 2-nonyne, 317 1,4-benzohydroquinone, 1477 2-oxazoline, 2529 1,4-benzoquinone, 1477, 123,2042,2044 2-picoline, 2998 1,4-dimethoxybenzene, 1128 2-pyridinealdoxime, 2734 1,4-dioxygenation, 1675 2-pyrroline, 2529 1,4-hydroquinone, 1055, 1477, 1841 2-tetrahydroxybutyl-quinoxaline, 2084, 2086 1,4-naphthoquinonedibenzene-sulfonimide, 2-thiohydantoin, 2488, 2489, 2490, 2858 2147 2-vinylbutadiene, 1014 1,4-pentadiene, 1519,2881 2-vinyloxetane, 308 1,5-cyclooctadiene,803 2-vinyloxirane, 308 1,6-naphthyridine, 2335 2-vinylphosphirane,2881 1,7-dihydroxynaphthalene, 553 2,2-diethoxypropane, 200 1 1,8-naphthalenediamine,2198 2,2,4,4-tetramethylpiperidine,3146 1,8-naphthyridine, 1138 2,2' -dibenzoyloxyacetophenone, 170 IO-ketodocosanoic acid, 422 2,3,5-triphenylimidazole, 2293 l O-phenanthroline, 1572 2,3,5,6-tetramethylacetophenone, 130 12-ketoergostane, 1857 2,4-dialkoxypyrimidine, 1408 12-ketopregnane, 1857 2,4-dimethylquinoline, 1139 17-hydroxy-20-ketosteroid,877 2,4-dinitrophenylacetone, 2017 17-keto-steroid,3158 2,4-dinitrophenylhydrazine, 1007, 1086, 1633, 17-oxo-steroid, 3158 1847, 1855 18-crown-6, 704, 737, 743, 1250, 1485, 1487, 2,4-dinitrotoluene, 1381, 1895 2008,2550,2782,2848,2976 2,4,6-trinitrotoluene, 1041 IH-l,2,3-triazole,905 2,5-dimethoxytetrahydrofuran, 667, 2415, 2416 2-acetidinethione, 1222 2,6-dinitroisovanillin, 136 2-acetylphenothiazine, 2188 2,6-diphenylmethyltetrahydro-4-pyranone, 2-alkenylthioanilide, 1164 1800 2-alkyloxazoline, 750 2,6-lutidine, 170, 1162, 1735,2462 2-aminopyridine, 631, 632, 753, 2891 2'-deoxyribofuranosylpyrimidine, 1408 2-aminothiophene, 1213, 1214 2'-hydroxychalcone, 53 2-azetidinone, 819, 1234,2636 2'-oxychalcone, 52 2-bromoethylphthalimide, 1178 20-ketopregnane, 2988 2-bromonaphthalene, 1969 2H-azirine, 1376 2-bromopyridine, 513, 753 3-alkoxyacetal, 2000 2-butene-l,4-, 1668 3-aminoacenaphthene,690 2-cyclopentenone, 2011 3-aminopyridine, 693, 921 2-hydroxyacetophenone, 54 3-benzyl-5-(2-hydroxyethyl)-4­ 2-hydroxyquinoline,692, 1639 methylthiazolium chloride, 14, 1938, 2-imidazoline, 2529 2665 2-imidazolinone, 2529 3-bromopropyne, 1038 2-iminohydantoin, 954, 955 3-chloroaniline, 907 2-isocyanostyrene, 1164, 1167 3-chloropseudocumene, 1531 2-methoxyquinoline,1713 3-ethylthiotetrahydrofuran, 537 2-methoxythiophene,491 3-furoic acid, 310 1 2-methyl-5-phenylsulfonylhydroquinone, 1422 3-hydroxycinnoline, 2022, 2023 2-methyl-6-phenylsulfonylhydroquinone, 1422 3-hydroxyquinuclidine, 275 2-methylindole, 1358, 1360, 1793 3-iodoanisole, 1912 2-methylterephthalic acid, 1381 3-methylalizarin,461 2-methylthiobenzthiazole, 1714 3-methylcyclohexanol, 119 SUBJECT INDEX 3633

3-methyleneindoline, 1719 acetogenin, 1609 3-methylisocoumarin, 1359 acetohydroxamate, 2489 3-oxoglutarate, 2968 acetolysis, 2931 3-phenylindene, 2884 acetomesitylene, 1750 3-phenylpropionaldehyde, 2175 acetonedicarboxylic ester, 2182 3-picoline, 2998 acetonide, 1279, 1280, 1281 3-quinuclidinone, 2570 acetophenone, 268,598,661,662,677,711, 3-quinuclidone, 275 874,912,995,1316,1675,1739,1860,1862, xaline,2084, 2086 3-thiazoline, 107, 108 2062,2074,2090,2188,2260,2491,2731, 19,2490,2858 3,4-lutidine, 3141 3012,3018,3019,3020,3034,3121,3137 3,5-dicyanodihydropyidine, 1321 acetoxylation, 2762 3,5-dinitrobenzamide, 1543 acetyl hexachloroantimonate, 849 4-aminoindole, 1254 acetyldemissidine, 2896 4-aminophenol, 191 cyclotrimerization, 2345 1 4-bromoindole, 1361 acetylene-allene rearrangement, 2864 ine,3146 4-ethylpyridine, 2998, 2999 acetylene, 93, 101, 181, 389, 391, 536, 606, enone, 170 4-hydroxyazobenzene, 2942 616,619,621,635,820,1032,1034,1151, 2293 4-hydroxycinnonline,474 1703,1710,1728,1779,2147,2234,2345, lenone, 130 4-hydroxyquinoline, 692, 693, 1252, 1253, 2347,2353,2358,2362,2363,2364,2365, 408 1638 2373,2450,2495,2548,2562,2793,2794, 39 4-iodoacetophenone, 1432, 2631 3018,3019,3020,3021,3148 2017 4-keto-3,4-dihydroquinazoline, 2054 , 616, 619,1032,2471,2629 ie, 1007, 1086, 1633, 4-methyl-aminoveratrole, 1417 acridine, 362,363, 364,2467, 2468, 2838, 4-nitrobenzenesulfenyl chloride, 70 2839,2872 1895 4-octanone, 677 acridizinium, 506, 511, 5 J2 L 4-picoline, 2482 acridone, 1572, 1731, 1732, 2838 uran, 667, 2415, 2416 4-quinolone, 692 acrolein, 176; 177,178,275,925,1621,1913,

) 4,6-dichlorobenzothiazole, 1395, 1397 2604,2873 ydro-4-pyranone, 5-bromomethylvanillic acid, 1482 acrylonitrile, 275, 919 5-enopyranoside, 1051 acrynitrile, 1908, 2307 735,2462 5-exo-dig radical cyclization, 1167 actinometry, 952, 953 imidine, 1408 5-forrnyl indane, 492 acutiphycin,47 5-hydroxyindole, 2042, 2043 acyclic metathesis polymerization, 57 5-methylisatin, 2188 acyl Pictet-Spengler reaction, 2210 5-oxazolone, 353 acyl transfer reaction, 168 5-sulfamoylisatin, 2188 acylbenzenesulfonylhydrazide, 1853 5,5-dimethylhydantoin, 1835 acyloin, 13, 14, 18,493,833,1317,1319 10 5,6-dimethoxy-l-indanone, 1128 acyloxyheteroarene, 1143 1 6-endo-dig radical cyclization, 1167 AD-mix-a, 2574, 2577 lyl)-4­ 6-oxadihydrouracil, 1408 AD-mix-,B, 2574, 2575, 2576 ride, 14, 1938, 8-hydroxquinaldine, 374, 375 Adams catalyst, 2780 9-bromomethylanthracene, 3070 additive Pummerer reaction, 2285 9-formylellipticine,724 additive seleno Pummerer rearrangement, 2286 9-methylanthracene, 3070 adipic acid, 364,1096,1097,1948,3116 1531 9-phenylfluorene, 1379 ADMET, 57, 58 n,537 aerosol, 766 absolute configuration, 1021, 1983, 1984, 1985 aglycon, 1046, 1408, 1410,1650,1843 2,2023 acenaphthylene, 820 aglycone, 1650, 2983 ~75 acetamidine, 2241 alcoholysis, 669, 677, 1473, 1872,2911 acetanilide, 1569,2092,2201 aldimine stannichloride, 2659 acetoacetic ester, 9, 25 aldimine,74, 1491, 1821,2660,2770 19 acetoacetone,688, 1038, 1422,1633,3130 alditol, 2718 3634 SUBJECT INDEX aldoketene, 822 allenic Pauson-Khand reaction, 2132 aldol reaction, 45,858,1022, 1187,1299, 1305, allenylation, 1779 1383,1508,1606,2523,2697,2783,2785 allenylsilane, 837 aldol-Tishchenko reaction, 2783, 2784 allocyathin, 1367 aldonamide, 2946 allyl furohydroximate, 3045 aldonic acid, 2446 allyl sulfenate, 1952 aldononitrile, 3056, 3057 allyl sulfoxide, 1064, 1952 aldose, 74, 75,1403,1404,1613,1614, 1763, allyl tri-n-butylstannane, 1597 2400,2446,2852,3056,3057 allylation, 1187, 1491, 1492, 1777, 1778, 1779, aldoxime, 376, 2017 2799,2812,2813 aleuritic acid, 2865 allylethylamine, 147 a1foI1214,3134 allylic oxidation, 2395, 2396, 2476 alfol 6, 3134 allylsilane, 683, 837, 1103, 1491, 1803 alfol 8, 3134 allylstannane, 837, 2679 aliphatic S-N Smiles rearrangement, 2611 allyltriisopropylsilane, 837 Alizarin Bordeaux, 461 allyltrimethylsilane, 1491, 1492,1493,2373 Alizarin Cyanin Black, 461 altohyrtin A, 1021, 1288 Alizarin Cyanine R, 461 aluminum isopropylate, 1288 Alizarin Green S, 461 amberlite 1R-120, 2949 alkenylsilane, 3100 amberlite IR-4B, 1622 alkoxy ethylenimine, 2018 amberlite IRA-4oo, 1622 alkoxy radical fragmentation (ARF), 2718 amentoflavone, 2983 alkoxyketene, 308 amidation, 25, 2399, 3186 alkoxyphosphorane, 1955 amidine, 288,2233,2234,2239, 2241,2243, alkoxysilane, 3146 2294 alkoxysulfane, 1929 amidoalkylation, 1443,2808 alkyl dinitrone, 2221 amidoxime, 2773 alkyl imidate, 1713 amidrazone, 2242 alkyl phthalimidoacetate, 1183 aminal, 1069 alkyl selenoxide, 2548 amination,315,544, 554, 1009, 1358, 1359, alkyl sulfonate, 2707, 2708 1360,1569,1737,2303,2771,2799 alkylaniline,924, 1194 aminoalcohol, 1222, 1384, 1808,2779 alkylation, 9, 181,215,411,416,863,930, aminohydroxylation, 2568, 2569, 2570 939,974,978,993,1001,1036,1120,1131, aminoketene, 308 1132,1176,1314,1342,1418,1469,1811, aminolactol, 3032 1913,1930,1955,1983,2164,2290,2303, aminolysis, 353,445, 1222 2336,2523,2695,2697,2799,2807,2998, aminophenol, 191,498,499, 1622, 1745,2198, 3004,3027,3190 3186 alkylative decarboxylation, 1687 aminopolysaccharide, 75 alkylidenation, 1170, 1171 arninopyridine,631,693,753,921,2890,2891 alkylidene metallacycie mechanism, 3150 aminopyrimidine,497, 1408, 1410,2789,2890 alkylidene, 353,1321,2892,3148 aminostyrene, 142, 1165, 1358,3008 a1kylidenecyciopropane, 515, 516 aminotetrahydroquinoline, 1640 alkylnitrite, 1867,2868 aminotriazole, 2159 alkylphosphonic acid, 669 amozonolysis, 766 alkylsulfonamide, 946 amphidinolide A, 2680 alkynedicobalt hexacarbonyl complex, 2131 amphidinolide B I, 1021 alkynide, 717 amphotericin B, 1485 alkynolate anion, 1683 amyl nitrite, 1627, 1629 alkynone, 2963 androgen, 2988 allene, 536,808, 819, 821, 822,828,837,930, androgenic assay, 3158 1274,1719,2003,2132,2548 androsterone, 3160 SUBJECT INDEX 3635 ldreaction, 2132 angucycline, 507 arabinose, 1614, 1615, 1789,2446,2448,2852, anhalonidine methiodide, 991 2949,3056,3059 anil, 923, 1137,2385,2604,2673 arene, 1170,1496, 1861, 1862,1866,2049, anilide, 1144, 1638 3184 :e,3045 aniline, 116, 117, 142, 192,377,406,408,447, arenesulfinate, 1131 499,577,688,921,922,924,925,942,947, arenesulfonamide, 1418 , 1952 948, 1041, 1069,1080, 1140, 1165, 1193, arenesulfonate, 1131 ane, 1597 1194,1198,1252,1314,1359,1415,1418, argentic oxide, 723 1,1492,1777,1778,1779, 1458,1471,1554,1569,1572,1628,1629, aromatic diazonium tetrafluoroborate, 1248 1638,1717,2093,2245,2326,2328,2385, aromaticity, 848, 897, 1131, 1883,2514,2622, 2386,2387,2455,2504,2626,2651,2722, 2927,3009,3082,3179,3188 15,2396,2476 2726,3019,3060,3061,3062,3065,3066, aromatization, 900, 1345, 1477, 1504,2553, 1103,1491,1803 3130,3172 2892,2912 679 anilinotetrazole, 2904 arsenous chloride, 225 e,837 anionic [2,3]-sigmatropic rearrangement, aryl hydrazone, 1069, 1548 1491,1492,1493,2373 3049 aryl sulfonanilide, 1144 288 anionic N-Fries rearrangement, 1144 arylacetylene, 619 .te, 1288 anionic ortho-Fries rearrangement, 1144 arylarsenic acid, 224 49 anionic phospho-Fries rearrangement, 1144 arylarsonic acid, 2418 2 anionic thia-Fries rearrangement, 1144 arylenemandeloamide, 1076 622 anionic a complex, 1542, 1883 arylethylamine, 2210, 2211 anisaldehyde, 603, 2267 arylhydrazine, 1080, 1081, 1547, 1558 3186 anisaldoxime, 2260 arylhydrazone, 471, 1084, 1548 234,2239,2241,2243, anisole, 390, 702, 1979,2267,2268,2284, arylstibonic acid, 225 3027,3101,3116,3130 arylsulfonate, 1144 3,2808 anomeric interaction, 1392 arylsulfonylurea, 3065 ansa-metallocene, 820 as-triazine, 2242 , 91, 93, 901, 982, 1227, 1867,2368 asimicin, 1609 anthracenedione, 2368 aspidophytine, 1165 ;54,1009, 1358, 1359, anthranilarnide, 1200 atacticity, 3146 ~303, 2771, 2799 anthranilic acid, 497, 629, 1399, 1402, 1569, atom transfer radical polymerization, 3012 384,1808,2779 1731,1732,2054,2055 atropine, 2415 Z568, 2569, 2570 anthranol, 179 ATRP,3012 anthraquinone, 176, 177, 178, 179,459, 1227, autoclave process, 2817, 2819 1347,2570,2701 aza Wolff rearrangement, 3076 1222 anthrone, 177, 178 aza-[2,3]-Wittig rearrangement, 3049 l,499, 1622, 1745,2198, anti-Bredt's rule, 525, 822 aza-[2,3]-Wittig sigmatropic rearrangement, anti-Brook rearrangement, 529 3049 75 anti-Markovnikov rule, 1833 aza-2,3-Wittig rearrangement, 3049 )3,753,921,2890,2891 anti-Markownikoff addition, 536, 1833 aza-Brook rearrangement, 529 .1408,1410,2789,2890 anti-Markownikoff product, 1834 aza-Darzens reaction, 841 55, 1358, 3008 anti-Markownikoff rule, 1833 aza-di-7l'-methane rearrangement, 910, 911 'ine, 1640 antiarrhythmic, 557 aza-Grob fragmentation, 1280 anticonvulsant, 557 aza-Henry reaction, 1383 antidiabetic, 557 aza-heterocycle, 515 antihydrol,2818 aza-Mannich reaction, 1820 antimalarial, 25, 474 aza-Michael addition, 1922 antiperiplanarity, 2931 aza-Myers-Saito cyclization, 2004 9 aplyronine A, 1021 aza-Pauson-Khand reaction, 2132 apomorphinium, 1452 aza-Payne rearrangement, 2139, 2140 Appel agent, 95 aza-pinacol rearrangement, 2228 Appel reagent, 95 aza-Robinson annulation, 2405 3636 SUBJECT INDEX aza-Wittig reaction, 3031, 3032 1385,1390,1491,1493,1580,1622,1624, azadiene, 506, 1668, 1669,2637 1789, 1800, 1801, 1802, 1816, 1818, 1894, azaindole, 229 1948,2078,2088,2090,2160,2161,2162, azene,2730 2224,2257,2260,2271,2282,2293,2432, azepan-4-one,516 2504,2615,2687,2688,2711,2785,2791, azepinone, 1622 2940,3012,3018,3033,3034,3121 azetidine, 1180, 1181, 1222 benzaldimine, 2221 azetidinethione, 1222 benzaldoxime, 2260, 2262, 2676 azetidinimine, 1222 benzamide,2575,2900,2911 azetidiniminium salt, 1222 benzamidine, 1754,2235,2241 azetidinone sulfenic acid, 1979 benzamidoxime, 2773 azetidinone, 522, 2636 benzannulation, 934, 2514 azido Mannich reaction, 1820 benzanthrone, 176, 177, 178, 179, 180 azido-Mannich reaction process, 1820 benzazepine, 1155 azidolysis, 2799 benzazole, 1883 azidotrimethylsilane, 2506, 2850 benzenediazonium chloride, 947, 948, 2471 azine, 3084, 3085 benzenesulfonic acid, 2518, 2822, 2823 aziridine, 714, 872, 1180, 1181, 1184, 1434, benzhydryl, 1347 1435,1504,2139,2140,2228,2229,23, benzhydrylamine, 1224 3020 benzidine, 320 azirine, 1434,2017,2018 benzil, 326, 327, 328, 332, 996, 1428,2293, azlactone, 353, 354, 355, 356, 832, 833, 997, 2295,3001 998,2656 benzimidazole, 2197, 2198, 2335 azoarene, 284 benzimidazolone, 304 azobenzene, 323,2471, 2944 benzisoxazole, 1605, 1607 azoimide, 2503 benzocarbozole, 1559 azomethine, 964, 965 benzocinchoninic acid, 923 azotometer, 105 benzodiazepine, 2831 azoxyarene, 284 benzofurazan N-oxide, 303 azoxybenzene, 2942, 2943 benzofuroxan, 303, 304, 305 aztreonam, 2636 benzoin, 13, 14, 18,331,332,855,996,2799, , 837, 2185,2186, 2187,3139, 2888,2890,2891,3001 3141 benzonitrile, 151,273,362,1284,1989,2241, azulenone, 563, 564 2335,2399,2504,2900,2901,2902,2903, 2911 bafilomycin AI, 1021 benzophenone oxime, 93 Bakelite, 160, 161,429,3183 benzophenone,93,578,677, 714,1254,1314, Bakelizer, 160 1379,1737,1872,2062,2128,2260,2676, barbiturate, 1811 2965 barbituric acid, 558 benzoquinolizinone, 516 barrelene di-n-methane rearrangement, 910 benzoquinone, 303, 1041, 1358, 1359, 1361, Barton-Hunsdiecker decarboxylation, 1512 1477,1923,2042,2044,2369,2462,2701, batzelladine, 380 2762,2848,2921,2922 Be. Acid, 2822 benzosuberone, 1127 Beckwith-Honk transition state model, 2827 benzosulfohydroxamic acid, 83 beef tallow, 2819 benzothiazepine, 2766 benzalaminoacetal, 2256, 2257 benzothiophene,267,406,407,820,2421 benzalcoumaranone, 53 benzothiozole, 1395, 1396 benzaldehyde, 14,25,29,48, 151,205,277, benzoylene urea, 2054 278,331,333,353,374,375,377,382,443, benzoylhydroperoxide, 2270 453,545,603,661,662,715,722,863,864, benzpinacol, 2128 912,923,999, 1070, 1209, 1211, 1314, benzyl N-sulfamoylcarbamate, 1132 SUBJECT INDEX 3637

~O, 1622, 1624, benzylamine, 89,441,571,572,573,2109, brornolactonization, 1521 16,1818, 1894, 2901,3019,3074 bromomethane, 1511, 60,2161,2162, benzylaminoacetal, 441 bromotrichloromethane, ~38, 1512 82,2293, 2432, benzylcarbamate, 2143 brucine salt, 1829 11,2785,2791, benzylidenecyclopentanone,454 Bucherer-Strecker synthesis, 2710 34,3121 benzylidenecyclopropane, 1813 Bucherer-Strecker reaction, 2710 benzyne,507,570,571 Bucherer-Strecker synthesis, 2710 ;76 Bestmann modification, 2560 bullatacin, 1609 Bestmann ylide, 3031 , 811,1274,1275,1475,1693, n betaine, 1955, 1956, 3031, 3032, 3033, 3035, 1728,1729,1777,1943,2097,2098, 3150 2368,2968 Betti base, 374, 375 butenylcadmium,1230 179, 180 Betti's , 374 butyl nitrite, 475, 1629 Beyer method, 924 butyraldehyde, 1728, 1938, 2665 bifurcarenone, 2969 butyroin, 677 947,948,2471 Biginelli compound, 379 butyrophenone, 1857 2822,2823 bilane, 2430 bile acid, 433, 1593, 1940 C-H insertion, 562 bilin, 2430 cadmium reagent, 1230, 1231, 1232 binaphthol, 553, 2047 calicheamicin, 341 196,1428,2293, biophosphate, 2647, 2648 calix[ 4]arene, 2922, 3184, 3185, 3187, 3188, biphenylene, 388, 2389 3190 2335 bipyrrin, 2430 calix[n]arene, 3184, 3185, 3186, 3187, 3190, biquinoline, 2605 3192 Birch reductive alkylation, 390 calixcrown, 3184 Birch rule, 388 calixcyclitol, 3186 bis-lactim ether, 2523 callipeltoside A, 2680 bis(cyclopentadienyI)zirconium(IV) chloride calomel, 952 hydride, 2540, 2541 camphene, 370, 1692,2392,2400,2932 >5 bis[trimethylsilyl]peroxide, 151 campholic acid, 2930 12,855,996, 2799, bisdimethylaminoacetone, 557 camphorcarvone, 820 bisimidylurea,2241 camphorsulfonic acid, 1048 ,1284,1989,2241, bisvinyIhydrazine, 2218 camphorsultam, 2132 2901, 2902, 2903, Blaise reagent, 420 canescin, 1701 BMA process, 81 caproamidine, 2241 boric acid, 211, 301,459,942, 1351,2084, caprolactone, 151, 1014 7,714,1254,1314, 2085,2603,2782 carbamate, 442, 571,1144, 1222, 1443,2143, ,2128,2260,2676, bornylene, 643 2392,2538,2568,2569,2957 boromycin, 624, 625 carbamic acid, 780 borono-Mannich reaction, 1820 carbazole, 238, 315, 471,472,549,550, 1070, 1358,1359, 1361, boroxine, 2735 1146, 1256, 1326, 1558, 1884,2363,2390, ,2369,2462,2701, brassilexin, 2875 2730,2872 brevitoxin B, 1723 carbene, 195,308,529,562,563,575,799, bridgehead carbon, 525 817,930,934,936,1064,1066,1068,1172, id,83 bromal, 2168 1314,1315,2089,2132,2185,2186,2560, bromination, 25, 465,1371,1372,1512,1940, 2657,2734,2884,2909,3074,3075,3095, ,407,820,2421 2264,2472,2896,3067,3068 3096 bromoacetate, 398, 426, 1234 carbenoid, 842,930, 1151, 1152, 1274,1767, bromoacetophenone, 857, 2059, 2060 2594,2595,2753,2754 t70 bromocresol, 421 carbinol, 91, 210, 212, 218, 455, 501, 734, 735, bromofluoroacetate, 2315 993,994,1461,1609,1983,2115,2206, mate, 1132 bromohydrin, 1674 2336,2431,2718,2892,2937,3020 3638 SUBJECT INDEX carbinolamine, 1305 chloranil, 471,551,2431,2432 carbobenzoxy group, 358, 359 chlorin, 2429 carbocation, 182,407,776,848,869,877,900, chlorination, 96, 98, 271, 846,1198,1371, 901, 1060, 1131, 1132, 1469, 1496, 1642, 1372,1395,1396,1748,1912,2092,2094, 1656, 1834, 1867, 1894, 1972,2039,2049, 2299,2311,2472,3069,3179 2227,2228,2248,2264,2326,2399,2442, chloroacetonitrile, 1915,2722,2724,2728 2503,2506,2718,2778,2808,2813,2901, chloroethene, 2793 2930,2931,2932,2989 chloroformate, 391,416,442,848,1131,2338, carbocycle, 683, 837, 838,2115 2538,2897,2898,2957,2960 carbodiimide, 822,1601,1773,2132,2774, chloroformylation, 2873 2904,3032 chlorohydrin, 2989 carbometalation, 2595 chloromesitylene, 1531 carbometallation, 2029 chloromethyltrimethylsilane, 669, 671, 3095, carbon single-wall nanotube, 389 3097 carbon tetrachloride, 95, 96, 97, 98, 114, 116, chlorophosphonation, 673 298,328,644,801,1339,1512,1526,1544, chloroprogesterone, 112 1637,1644,1747,1847,3068,3164 chloropurine, 2734 carbonamide, 3018, 3021 chloropyridine, 522, 667, 2330, 2734 carbonimidic dichloride, 2897 chloropyrimidine, 2734 carbonylative Stille cross-coupling, 2678 chloroquinoline, 2330, 3165 carbonylcyclopropane, 2881 chloroquinone, 1055 carbosugar, 1051, 1052 chlorosulfite, 1131 carboxamide, 315,1311,2569 chlorosulfonic acid, 1418 Carius tube, 863 chlorotriazine, 2734 camegine, 442 chlorotris(triphenylphosphine )rhodium (I) carotene, 1930 complex, 30 II carumonam, 2636 chlorotris(triphenylphosphine)rhodium (I), carvenone, 2994 3011 castor oil, 2373 cholestane, 2988 catalytic asymmetric Sharpless carbamate cholesterol, 847 aminohydroxylation, 2568 cholesteryl chloride, 847 catalytic asymmetric Strecker reaction, 2710, choline, 3185 2712 chromatic acid chloride, 1017 catalytic asymmetric Strecker synthesis, 2710 chromene, 2983, 2984,2986 catechol, 830, 1055, 1817, 1861 chromic acid, 93, 213, 1564, 1699,2861 catecholborane,537, 589,590,591,734, 3012 chromium carbene complex, 934, 2884 catharanthine, 1165 chromone, 168, 1679, 1680,2151 CBS catalyst, 709, 710 chromyl chloride, 1017 cephalosporin, 1979,2636 chrysin, 1146, 1903 cerium chloride, 1782, 2544 Chugaev reaction rule, 642 chalcogen iodine complex, 1521 CIDNP, 3044, 3075 cha1cogenide, 275 cinchona, 1237, 1675,2316,2568,2575,2712, chalcone, 53, 660, 661, 662, 1583, 1585, 1923, 2785,2975,2976 2188,2399,2975,2976,2978,2983,2984 cinchonidine, 1830,2977 Chan-Lam-Evans modified Ullmann cinchoninaldehyde, 604 condensation, 1572 cinchoninic acid, 604, 922, 2188 chelator, 83, 2484 cine-substitution, 2678, 2804 chlolesterylene, 643 cinnamaldehyde, 722, 1314, 1998, 2698 chloral, 2168, 2170, 2422, 2467, 2468, 2469, cinnamate, 1144,2201 2493,2783 cinnamic acid, 471, 472,820, 1512, 1513, chloramine, 1110, 1111 2161,2162,2807,2864,2946 chloramines-T, 2569 cinnoline, 474, 2908, 2909, 2910, 3008, 3009 SUBJECT INDEX 3639

cis-cyclooctene, 2128 cryptand, 388 cis-dihydroxylation, 2574 cumene hydroperoxide, 2975 71, cis-jasmone, 1510 cuprene, 2360 2094, citraconic acid, 2147 cuscohygrine, 1566 citronellal, 1621 cyanamide, 32, 780, 781, 2774, 2896 '28 civetone, 438, 439 cyanation, 2426, 2710, 2711, 2896 clavicipitic acid, 571 cyanic acid, 3064, 3065 l,2338, c1aycop, 1893, 1895 cyanoacetamide, 1294, 1296, 1621 Clorox, 1112 cyanoacetic acid, 1294 , 68, 1083. 1098, 1351, 1516, 1517, cyanogen bromide, 2896, 3173, 3174 1535,1834,1893,2051,2132,2303,2345, cyanogen, 424, 2905 2346,2348,2352,2358,2455,2657,2658, cyanohydrin, 557, 559, 722, 723, 724,1076, 3095, 2931,3135 1613,2710,2770,2771,2777,2778,2852, cocaine, 2415 2853 collidine, 635, 636,1321,1845,1953,1954, cyanotrimethylsilane, 559 2429,2430,2847 cyanuric chloride, 2873, 2957, 3186 conical intersection, 2126 cyaphenine, 2902, 2903 conjugated addition, 1922, 2524, 2695 cyclic model, 756 contra-Markownikoff rule, 1833 cyclic orthoester, 1217 (I) 2-thiophenecarboxylate, 1755, 1756 cyclic thionocarbonate, 746 Corey-Bakshi-Shibata catalyst, 709 cycloadduct, 43, 516, 517, 806, 821, 822, 886, Corey-Chaykovsky reagent, 713 887,1851,2348,2368,2675 Corey-Hopkins methodology, 746 cycloalkenone, 1803 Corey-Hopkins protocol, 746 cyclobutabenzofuranone, 1312 (I) Corey-Kim Reagent, 726 cyclobutane, 823, 1113, 1114, 1124, 1803, Corey-Suggs reagent, 742 2164,2544 (I), Cornforth model, 756 cyclobutanol, 858, 2067, 2068, 2463 corrole, 2429, 2431 cyclobutanone, 307, 1027, 1221, 1274.2711 corticoid, 1403 cyclobutene, 43, 820 corypallin,410 cyclodextrin, 1144, 1606,2062,2922,2975, Cossee mechanism, 3148 3184 Cossee-Arlman mechanism, 3148 cycloheptadienone, 799 cotarnine, 410 cycloheptatriene, 562, 563, 2185 coumarin, 220, 221, 222, 820, 977,1146, 1622, cycloheptene, 851 il 1679,1722,2151,2153 cycloheptenimine, 1182 Cram product, 756 cyclohexadienate ion, 1542 Cram-Reetz rule, 757 cyclohexadiene, 341, 343, 527, 887, 940, 1441, Cram's chelating model, 756 1849,1967,2515,2621,2622,2799 Cram's model, 756 cyclohexadienone, 900, 2330, 2892 Cram's rule selectivity, 756 cyclohexanemethylamine, 870 Cram's rule, 756 cyclohexenone, 858,1584,1923,2552 '5,2712, crambescidin, 380 cyclohexylphosphonyl chloride, 675 crambine, 380 cycloketone, 434, 742, 939 cresol, 183, 1886,2329,2454,3178,3179, cyclooctanedione, 858 3180,3184 cyclooctanol, 762 Criegee intermediate, 770 cyclooctatetraene, 2346, 2358, 2359, 2360 cross metathesis, 57, 58 cyclooctene, 851, 2038, 2128 18 crotonaldehyde, 301. 302, 927, 1622, 1728, cyclopentadiene, 887, 1948, 2346, 2367, 3141, 1729,2097 3142 513, crotyl chloride, 1779 cyclopentane, 1113, 1114, 1124, 1803,2544 crotylboronate, 2435, 2436 cyclopentanone, 313, 433, 434, 732, 1113, 8,3009 croty lsilane, 1492 2188,2212,2687,2697,2971,3158 3640 SUBJECT INDEX cyclopentene, 2131, 2880, 2881, 2882, 2883, desilylation, 837, 1103, 2622, 2629, 3052 2884,3152 desoxybenzoin,2686 cyclopentenocycloheptanone, 2185 desoxymorphine, 2267 cyclopentenone, 934, 935, 1508, 1509,2011, Dess-Martin oxidant, 871 2013,2014,2131,2132 Dess-Martin Periodinane reagent, 871 cyclophosphamide, 2647 Dess-Martin reagent, 871 cyclopropane, 515, 517, 714,910,911,1048, desulfonation, 1531 1064,1123,1124,1617,1618,1834,1853, desulfurization,439, 1165, 1191, 1194, 1731, 2148,2164,2594,2687,2880,2881,2882, 1872,2302,2303,2789,3164 2884 desymmetrization, 1675,2797,2798,2799 cyclopropanol, 680, 1707, 1709 dialkoxytitanacyclopropane, 1706 cyclopropylamine, 1707 dialkyl chlorophosphate, 114 cyclopropylidene,930, 1812 dialkylphosphite, 114, 1588,2280,2281 cyclopropylimine,912 diaminonaphthalene, 553 cyclopropylketimine, 2881 diamond, 2772, 3095, 3096 cycloreversion, 516, 2127, 2369 diaryl, 982, 993, 1248,2126,2680 cyclosativene, 2931 diarylacetylene, 1151,2129 cyclotetramerization, 2358 diaryliodonium salt, 1910, 1911 diarylmethane, 132, 133, 134 D-model, 1274 diarylsulfoxide, 1841 dactylolide, 1485 diarylthiocarbonate, 1743, 1744 damirone, 571 diarylthiophene, 267, 268, 3019 Danishefsky's diene, 1991 diazine, 609, 1076 daphnicyclidin D, 2253 diazoacetophenone, 2058 DDQ, 1046, 1342, 1426, 1428,2430,2431, diazoaminosulfinate, 946 2964 diazoketone, 104, 564, 1110, 1111, 1112, 1683, deacetoxycephalosporin, 1979 2058,3073,3074,3075,3076 deacidite, 1622 diazomethane, 103, 104, 105,522, 1288, 1289, dealkylation, 2896, 2897 1617,1618,1619,1683,1812,2058,2059, decalin, 2370, 2455, 2731 2060,2147,2148,2149,2186,2491,2493, decarboxylation, 6,9,21,22,25,30,233,259, 2986,3164 402,437,525,677,780,832,881,892, diazonamide A, 624 1113,1252, 1314, 1388, 1443, 1444, 1477, diazonium tetrafluoroborate, 185,973, 1248, 1570,1605, 1646, 1656, 1687, 1688, 1700, 1249,1250,1628,2736 1812,1829,2054,2185,2303,2341,2446, diazotization, 185,475,868,879, 1080, 1267, 2503,2504,2702,2767,2968,2971,3019 1268,2022,2322,2777,2908,3009 decinine methiodide, 991 dibenzocarbole, 549 Degussa process, 81 dibromoalkene, 718 dehalogenation, 25, 308, 939, 1271, 1272, dibromocarbene, 930 1330,1570,2302,2842,2847 dibromomethyllithium, 1683 dehydrobufotenine, 571 dichlorophosphine, 2540 dehydrogenation, 21, 22, 215, 216, 217, 218, dichloroselenurane, 96 410,572,635,1298,1299,1302,1321, dicobalt octacarbonyl, 2131 1342,1693,1728,2097,2147,2185,2186, dicobaltoctacarbonyl, 1517 2206,2411,2455,2495,3159 dicyanobenzene, 391, 1464 dehydroxysilylation, 2463 dicyclohexylboron chloride, 48 Dennis-Bull process, 2822 dicyclohexylethylamine,489 deoxo-Fluor, 2957 dienophile, 506, 562, 606, 607, 886, 887, 916, deoxoartemisinin, 2300 1668,1669,2367,2368,2926 deoxybenzoin,974, 1215, 1903 diethyl zinc, 101, 1116 desacetoxycephalosporin, 1979 diethylaluminum cyanide, 2007, 2714 deselenization, 2303 diethylcyanophosphonate, 3105 SUBJECT INDEX 3641

,052 difluoroallene, 821 disproportionation, 45, 57, 320, 602, 1132, dihalophosphine, 1849, 1850 1379,1380,1530,1657,1747,1750,1751, dihydro-Reissert compound, 2335 2540,2782,3094,3095,3096 dihydrofuran, 837,1036, 1037,2026,2799, disulfone, 1787 2881,2884 disulfonylamide, 1418 dihydroisoquinoline, 411, 2335, 3139 dithiane, 316, 2963 dihydronaphthalene, 478, 479 dithiirane, 1723 '4,1731, dihydrooxepin, 2883 dithioacetal, 822, 1787 dihydropyran, 1114, 1217,2368 dithiocarbamate, 1330 2799 dihydropyrazine, 1302 dithiolethione, 1722 dihydropyridine, 1321,3140,3174 dithiopyrone, 2348 dihydropyrimidine, 379,1757 divinylmethane,910 Z81 dihydropyrrole, 391, 1504,2882,2884 Divuslon,2819 dihydroquinoline, 892, 1284, 2335, 2385, dodecylurea, 1089 2604 Doebner-von Miller quinoline synthesis, 2603, diisobutyl phthalate, 3146 2605 diisopropylcarbodiimide, 165, 1487, domino reaction, 2831 2654 Dowtherm, 1254,3183 diisopropylethylamine, 84, 523,1452, 1454, duroquinone, 138, 2893 1977,2649,2960 dynemicin, 341 diketoimine, 2540 dysidiolide, 2680 diketopiperazine, 2831 dimethyl acetylenedicarboxylate, 43, 123,695, Eaton's reagent, 1070 895, 1505 educt, 2831 dimethyl suberate, 1319 electrocyclization, 934, 3139, 3140 112,1683, dimethylacetylcyclohexene, 851, 2038 electrofuge, 288, 1279,2011 dimethylalkoxysulfonium salt, 726, 2193 electrolytic decarboxylation, 1443 288,1289, dimethyldichloroselenurane, 97, 98 electron-donating group, 387, 388, 602, 627, 58,2059, dimethylsulfoxide, 76, 1528, 1672,2118 765,776,777,778,822,886,925,977,993, 91,2493, dinitrogen tetraoxide, 2260 1064,1126,1127,1131,1132,1151,1194, dinitromethane, 2260, 2758 1252,1388, 1664, 1772, 1834, 1853, 1856, dioxaborolane, 2595 1866,1894,1897,2011,2076,2151,2210, '3,1248, dioxacarbazole, 1675 2218,2228,2251,2256,2368,2439,2504, dioxetane, 1676 2637,2673,2734,2808,2844,2847,2873, 180,1267, dioxindole, 1838 2883,2888,2896,2901,2930,2931,3008, 09 dioxirane, 1279,2590,2591 3172 dioxocin, 3179 electron-withdrawing group, 9,390,506,516, dioxolenone, 858 602,619,693,756,765,776,777,778,817, diphenyl diselenide, 831, 1466 821,886,925,942,977,1131,1176,1195, diphenylacetylene, 616, 799 1213, 1248, 1252, 1485, 1535, 1552, 1569, diphenylamine, 362, 364, 2838 1621,1664,1675,1772,1792,1834,1866, diphenylethane, 93, 181 1883,1897,2039,2100,2143,2176,2211, diphenylformamidine,2157 2241,2256,2270,2285,2322,2368,2439, diphenylmethane, 673, 974, 1379 2504,2533,2548,2609,2621,2637,2734, diphosphorus tetraiodide, 1703, 1704 2735,2744,2808,2883,2931,3008,3032, dipolarophile, 916, 1504, 1505 3043,3050 dipole rule, 120 Emde product, 989 ,887,916, directed Nazarov cyclization, 2011 enamine, 258, 259, 303, 304, 313, 353, 507, disaccharide, 1046, 1338, 1593, 1595, 1950, 690,1222,1305,1306,1322,1326,1327, 2983 1404,1675,1676,1821,1988,2210,2346, 14 discodermolide, 1022 2348,2487,2695,2696,2697,2767,2793, diselenide, 2303 2812,2964,3140 3642 SUBJECT INDEX enarrlinollidehyde, 1722, 1889 ethyl o-pelargonylpelargonate, 7 enaminone, 288, 516,1622 ethyl a,y-diphenylacetoacetate, 7 enarninothioaldehyde, 1722 ethyl s-benzamidocaproate, 25 enaminothioketone, 1722, 1725 , 183,267,268,269,677,678, enantio-discrimination, 2797 1700,3095 endo-cyclization, 2173 ethylchloroformate, 105, 2898 endoperoxidation, 1676 ethylene, 181, 183,317,517,789,887,1516, endoperoxide, 1675, 1676,2799 1728,1747,2368,2454,2920,3115,3134, ene-diol, 14 3136,3144,3146 enediol, 1404, 1564,2889 ethylenediamine, 315, 317, 537,1759 enediyne, 341, 343 ethylenedithioketal, 439 eneyne-allene, 2003 ethylenimine, 1434 enolization, 45, 525, 858, 1404, 1605, 1767, etiocholanolone, 3160 1795,1964,2160,2314 Eu(fodh,68 enolsilane, 122 Evans model, 757 enone,275,312,591,820,821,851,1155, Evans reagent, 1021 1583,1584,1722,1767,1845,1923,2014, Evans-Tishchenko 1,3-diol synthesis, 2782 2038,2844,2975,2976,2977 Evans-Tishchenko reaction, 2782, 2783, 2784, enophile, 37, 38, 1692 2785 enthalpy, 119,2003,2367,2368 Evans-Tishchenko reduction, 2782 enthaterumalide, 3110 excimer, 821 envirocat, 1127 exciple, 821 enynarrline, 820 exciplex, 820 enyne-mlene,2oo4,2514,2515 exciplexes,2127 enyne, 1535, 1967, 1968,2004,2134,2451 exo-calixarene, 3187 Epal process, 3136 epichlorohydrin, 1877 famesal, 722 episulfide, 249. 252 fats, 2817 episulfone, 2298 Fehling test, 1615 epothilone, 59 Felkin-Ahn model, 756, 757 epoxidation, 713,1534, 1535, 1536, 1537, Felkin's model, 756, 757 1583,1584,1585,2270,2271,2272,2442, ferrocene, 173,888,2737,3186 2580,2581,2590,2591,2975,2976,2977, ferrocenylideneamine, 2221 2994 Fetizon's reagent, 1055 epoxide, 53, 619, 713,1217,1452,1584,1812, fibrinogen, 557 1841,1880,1882,1967,2007,2139,2140, Fischer carbene complex, 934, 1064 2778,2865,2932,2933,2975,2976,2979, flash vacuum pyrolysis, 1014,3073 2990,2995 flash vacuum thermolysis, 516 eremomycin sulfate, 957 flavanone, 53, 660, 661 esperamicin, 341 flavazole, 2084 estrone, 2687 flavone, 52, 53, 54,168, 170,977,1722,1901, Etard Complex, 1017 1903,2983,2984 etherification, 2799, 2847, 3027 flavonoid, 2983 ethoxyacetylene, 100 flavonol, 53 ethoxymethyleneaniline,301 florisil, 97, 527, 728, 898, 899 ethyl benzoate, 995, 996,1250,3001,3146, fluoranthene, 3012 3147 fluorenone, 1245, 3085 ethyl isobutyrate, 6 fluorescence, 93, 364, 1530, 1795, 2928, 2929 ethyl isovalerate, 6 fluorination, 2744, 2745 ethyl sorbate, 256 fluorine, 185,822,2012,2744,2931 ethyl t-butylacetate, 6 fluoro-Pummerer rearrangement, 2285 ethyl rz-caprylcaprate, 7 fluorohydrin, 2989 SUBJECT INDEX 3643

fluorooxidizer, 2745 Gilbert-Seyferth reagent, 2559 fluorosilane, 532, 1430 gluconothiolactam, 1878 ftuorosulfate, 1131 glucopyranosylamine, 76 ,678, ftuorous phase, 379, 2831, 2832, 3014 glutaconic aldehyde, 3172 FMO,886 glutamic acid, 354, 1390 forensic toxicology, 1543 glutaric acid, 433, 1294 7,1516, formaldehyde, 132, 160, 161,429,430,443, glycal, 1046 5,3134, 468,56,602,603,807,1009,1011,2275, glycerol dynamite, 2817 2808,2809,3183,3187,3188 glycerol, 176, 178, 179,761,42,2303,2362, formanride, 490, 1457, 1737, 1738,2054,2056, 2603,2701,2817,2819,2860 2157,2503,2791,2872 glycol, 501, 761, 986,1032, 1290,2270,3090 formamidoxime, 2773 glycopeptide, 1046 formanilide, 2504 glycoprotein, 75 formhydrazide, 2157, 2159 glycosazone, 1083 formylation, 942, 43, 2330, 2789, 2872, 2873, glycosylamine, 76, 175 2874 glycosylation, 74, 1088, 1363, 1367,1408, 2782 forocidin, 873 1593,2498 83,2784, forward aza-Payne rearrangement, 2140 glyoxal, 1415,2286,2293,2295,2701,2969, forward thia-Payne rearrangement, 2140 2971 FRI82877,1485 glyoxaline, 2293 free radical clock, 1239 glyoxime, 2260 free radical, 1238, 1239, 1241, 1511,2046, glyoxylate, 478, 1388 2492,3075 glyoxylic acid, 1817 Fries-Rosenmund rearrangement, 1144 gonyautoxin, 424, 426 frontier molecular orbital theory, 886, 1422 gossypol,2818 fuchsonimine, 1242 green , 1777 Fukuyama sulfonamide protecting group, 1159 , 301, 422, 445, 446, 448, 450, fullerene, 820 487,489,490,521,571,1231,1232,1273, fullerenol, 122 1274,1276,1434,1706,1988,2406,2563, fulvene, 1967,2515 2963,3094,3130 fumaric acid, 1668, 1866, 2928 Grignard-Wurtz coupling, 3094 fumonisin 81, 1406 Grubbs catalyst, 57, 60, 2346, 2347, 2348 furfural, 603, 722 guaiacol, 443, 3168 furfuryl benzoate, 1014 guajene, 643 furoic acid, 3101 guanacastepene A, 2680 furoxan, 516 Guareschi imide, 1294 furoxane, 304 Guareschi product, 1294 Furukawa reagent, 2595 Guerbet , 1298 FVT,516 Guerbet surfactant, 1298 gymnomitrol, 2969 '22,1901, Gamer aldehyde, 1187, 1189, 1190 Gamer ester, 1187 H-ZSM-5 zeolite, 1893, 1894 gem-dichloroepoxide, 735 Haber-Weiss reaction, 1042 gem-dichlorooxirane, 735 Hajos-Parrish diketone, 1305 Gennari-Still phosphonate, 1486 Hajos-Parrish ketol, 1305 geranial, 722 Hajos-Parrish ketone, 1305 germane, 1238 Hajos-Wiechert ketone, 1305 m,2929 germanium-Peterson reaction, 2177 halfordinol, 1078 Ghosez reagent, 1221 halicholactone, 3109 Gibbs test, 2984 halo-Mannich reaction, 1820 ~5 Gilbert-Seyferth diazo phosphonic reagent, haloalkyne, 717 2559 halocresol, 3168 3644 SUBJECT INDEX halophenol, 3168, 3170 HOMO, 606, 821, 878, 886, 2271 halophile, 1650 homologation, 717, 1274,3073 halophilic substitution, 95. 114,2093,3164 homoveratric aldehyde, 637 halosulfate. 1131 Homer reaction, 3031, 3035 Hantzsch collidine synthesis, 1321 Hoveyda-Grubbs catalyst, 57 Hantzsch ester, 1321 Huang-Minlon method, 3084 haplophytine, 1165 Huang-Minlon modification, 589, 590, 3084, heat content, 119 3086 heavy wax, 1098 Huang-Minion procedure, 3084 Heck cyclization, 1350 Huang-Minlon reaction, 3084 Helferich condition, 1367 Huang-Minion reduction, 3084, 3085 helicene, 1860 Huang-MinIon Wolff-Kishner reduction, 3084 Hell-Volhard-Zelinsky chlorination, 1371 Hubner-Nolting-Komer rule, 775 hemiacetal, 14,2718,2784 Hunsdiecker-Barton decarboxylation, 1512 hemiaminal cyclization, 2107 huprine, 1138, 1139 hemibrevitoxin B, 1723 hydantoic acid, 2856, 2857 Hempel pipet, 2860 hydantoin, 557, 2711, 2856 hendecenoic acid, 1015 hydrastinine, 410 heptanoic acid, 2239, 2864 hydrazine, 31, 115, 251, 284, 549, 971, 1069, , 489 1070, 1073, 1080, 1082, 1176, III, 1262, HERON , 1392 1344,1345,1617,1619,1631,1699,1787, Herz compound, 1395, 1396 1789,1956,2084,2087,2157,2158,2219, Herz salt, 1395 2302,2799,2831,2994,2996,3084,3085, hetacillin sulfoxide, 1979 3086,3087 hetereobimetalJic, 1132 hydrazinolysis, 1176, 1177 hetem-Michael addition, 1922 hydrazobenzene, 320, 321,323 heteroannulation, 1137, 1717 hydrazoic acid, 2831, 2904 heterocyclic ring transformation (HRT), 750 hydrazone, 197, 572, 592, 1070, 1071, 1085, hexabenzocoronene, 2520 1547,1550,1552,1634,1635,1787,1821, hexachloroacetone, 96, 97 1845,1857,2043,2084,2085,2563,2564, hexahydrofluorenone,2778 2694,2770,2995,3084,3085,3086 , 389, 1923 hydridosilylketene, 3074 hexamethyldisilazane, I, 1411, 1685,2916 hydrindan, 1218 hexamethyldisiloxane, 1108, 1109, 1724 hydrindene, 429 hexamethylene tetramine, 865, 866 hydroalkoxycarbonylation, 2352 hexamethylenetetramine, 867, 942, 944, 2570, hydroanthraquinone, 178 2615,2616,2617 hydroazobenzene, 892 hexaphyrin, 2429 hydroazoic acid, 2503, 2504, 2506 Heyns product, 1403, 1404 , 536, 537, 1833, 1834,2799, Heyns rearrangement product, 1403 3012,3014 high temperature and high pressure (HTHP), hydrocarbalkoxylation, 2352 603 hydrocarboxylation, 2352 highest occupied molecular orbital, 886 hydrocinnamic acid, 471 Hinsberg test, 1418 hydrocinnamoyl chloride, 84 hippuric acid, 353, 997, 999 hydrocyanation, 2007, 2008, 2778 II

Hoch-Carnpbell product, 1434 hydrocyanic acid, 147,557,2337,2454,2771 U Hofer-Moest product, 1443 hydroesterification, 2352 il Hofmann exhaustive methylation, 1451 hydroformylation, 1070, 1071, 1516. 1517, u Hofmann rule, 1013, 1451, 1460, 1461,2480 2353,3012 iJ homo-Brook rearrangement, 529 hydrogen peroxide, 150, 151,263,265,452, homo-Favorskii rearrangement, 1027 454,540,829,831,978,1041,1103,1535, homo-pinacol coupling, 2221 1677,1948,1950,2084,27012975,3085 SUBJECT INDEX 3645

, 21, 22, 25, 284, 304,308, 340, 2540,2604,2636,2637,2638,2639,2673, 349,350,353,387,562,734,1634,1635, 2696,2702,2710,2711,2712,2754,2767, 1758,1759,1945,1946,1947,2072,2074, 2832,2965,3012,3031,3043,3085,3173 2143,2144,2257,2341,2421,2454,2455, imino 1,2-Wittig rearrangement, 3043 2456,2778,3011,3012,3014,3098,3134, imino ether, 1713, 2239 3185,3186 imino-Nazarov cyc1ization, 2012 },3084, hydrometallation, 2029 iminocarbene, 1256 hydroperoxide, 772,1438,1583,2580,2718, iminodiaza-phospholidine, 2101 2975,2976 iminophosphonate, 288 hydroquinone, 3, 303, 460, 508, 1041, 1055, iminophosphorane, 2642, 2643, 3031,3032 ; 1477,1841,2309,2360,2425 indabox ligand, 1385 ion, 3084 hydrosilylation, 1103,3012,3013 indan,1564 hydrotalcite, 151 indane, 2185

1, 1512 hydroxamic acid, 83, 263, 1772, 1773 indanone, 677 hydroxyanthraquinone,459 indazole, 2043, 2335 hydroxylamine, 288, 762,1403 indene, 479, 646, 934, 1885,2330 hydroxylamine, 81, 115,263,265,284,946, indigo, 136, 1227, 1399, 1401, 1402, 1751 1260,1593,2084,2467,2468,2773,2780, indium, 202, 205, 702, 704, 940, 1778, 1779, 171,1069, 2794,2831,3021,3056,3137 2315 11, 1262, hydroxynitrile, 2772 indole-2-carboxylic ester, 1375 599,1787, hydroxyphosphonamide, 730 indole, 140, 142, 143,228,258,259,406,407, 158,2219, hydroxypyridine,942, 1898 417,418,473,570,571,572,577,585,599, 084,3085, hydroxyquinoline, 598, 692, 693, 1252, 1253, 609,616,617,618,619,624,646,892,895, 1638, 1639 1055, 1069, 1070, 1071, 1164, 1165, 1167, hydrozirconation, 2540, 2541 1171,1172,1191,1192,1264,1265,1326, hydrozone, 1131, 1821 1358, 1358, 1360, 1375,1376, 1548, 1550, hyperbromite, 399 1552,1553,1622,1675,1676,1717,1718, D71, 1085, hyperconjugation, 993,1347,2881 1719,1791,1792,1867,1868,1869,1884, 1787,1821, hyperiodite, 399, 402 1922,1975,1979,2042,2248,2249,2255, Z563,2564, hypochlorite, 273, 1111, 1112, 1131, 1193, 2329,2330,2341,2342,2458,2722,2723, 3086 1194,1198,1200,1399,1535,1751,1841, 2730,2872,3174,3190 2571,2701,2946,2975,2977,3004 indolene, 2459 hypochlorous acid, 2092 indolenine, 2248 hypohalite, 248, 1447, 1448, 1511 indoline, 570, 571, 572, 585,1264,1548, 1976, hypoiodite, 1699, 1750 2873 hypophosphorus acid, 1165 indolizidine, 3074 hyrotalcite, 2630 indolizine, 275, 3076 16 indophenazine, 2467, 2468 834,2799, imene, 2730 inert free radical, 1239 imidate,629, 1027,1713,2242,2498 lng-Manske procedure, 1176 imidazole, 665, 772, 773, 1605, 1935,2293, Insectisol, 2423 2294,2295,2369,2530,2951,2957,3186 interrupted Nazarov reaction, 2011 imidazolidinone, 1997 intersystem crossing, 2062, 2127 imide, 81, 1923,2062,2115,2322,2807,2904 inverse Norrish type II rearrangement, 2068 78 imidine, 2237, 2238 iodination, 398, 2263 7,2454,2771 imidotitanium complex, 821 iodine, 398, 399,400,402,404,692, 720,871, imidylchloride,2904,2905 872,925,926,1174,1238,1247,1273, 1516,1517, iminazole, 2293 1474,1511,1521,1523,1629,1638,1750, imine, 205, 275, 288,442, 714,819,821,822, 1861, 1910, 1911,2264,2382,2386,2390, 63,265,452, 862,888,942,1009,1131,1222,1224,1234, 2454,2561,2596,2601,2602,2718,2719, 1,1103, 1535, 1235, 1383, 1403, 1406, 1491, 1588, 1589, 2720,2749,2823,2842,2875,3090,3091, 112975,3085 1813, 1820, 1821, 1823,1991,2210,2484, 3092,3168 3646 SUBJECT INDEX iodoaniline, 1165, 1569,1717,1718,1719, isopropanol, 27,803,1104,1176,1177,1481, 1720, 1977 1871,2072,2074,2237,2302,2454,2738, iododifluoroacetate, 2315 3077 iodoferrocene, 2844 isopropylbenzene, 1211, 1700 iodoform, 136, 1512, 1699, 1750, 1751, 1752, isoquinaldinic acid, 1314 2748,2749,2750 isoquinoline Reissert compound, 2335 iodohydrin, 1474 isoquinoline, 315,411,441,442,507,544, iodolactonization, 1521, 1522 545, 547, 1183, 1184. 2206, 2256, 2257, iodomethane, II, 853, 2040, 2670, 3141 2335,2336,3139,3172,3174 iodonium dicollidine perchlorate, 1521 isoquinolinium, 506, 507 iodonium dicollidinium perchlorate, 1046 isoquinolone, 192 iodosobenzene, 1910, 1911 isoschaftoside, 2983, 2984 iodosultinization, 1522 isosmaragdyrin, 2429 iodosylbenzene, 1535, 1539, 1647, 1648,2718, isotactic index, 3146, 3147 2719 isotactic polymer, 3145, 3146, 3147 iodoxybenzene, 1910, 1911, 1912 isotacticity, 3146 isatin, 1194, 1572, 1621,2024,2188,2315, isourea, 2652, 2896 2467 isovaleraldehyde, 1307 isatinate, 2188 isovanillin, 2688 isoamyl chloride, 465 isovitexin, 2983, 2984 isoamyl nitrate, 147 isoxazole, 624, 837 isoamyl nitrite. 1111, 1628 isoxazolidine, 515, 516, 517 isoandrosterone, 3160 isoxazolone, 376 isobomeol, 370 itaconate, 2686, 2687 , 1642, 1692, 2392, 2394 isobutyraldehyde, 300, 302, 391, 635, 1622, Jacobsen-Strecker reaction, 2711 2786 Janovsky adduct, 1542 isocamphane, 2931 Janovsky complex, 1542, 1543, 3159 isocarbostyril, 193 Janovsky product, 1542 isochroman, 2617 jervine, 3130 isocomene, 2969 Jones reagent, 1564, 1566 isocyanante, 1972 justicidin B, 1057 isocyanide, 254,255,256,547,972, 1457, 2121,2124,2458,2460,2529,2531 Karabatsos' model, 756, 758 isoflavene, 677 Katsuki-Sharpless catalyst, 2580 isoindazole, 2908, 2909 KCs, 1170, 1171, 1172, 1173, 1174 isoindole,255, 1075 kedarcidin, 341 isolauric acid, 2930 Kemp decarboxylation, 1605, 1606 isomerase, 1763 ketal, 899,1120,1172,1634,1782,1841,2221, isonicotinic acid, 1314, 3000 2223,2711 isonitrile, 11,561,1164,1457,1458,1661, ketazine, 2217, 2218, 2220, 3085 2017,2121,2122,2123,2529,2830,2831, ketene silyl acetal, 822,1821,1991,1996 2832,2833,3130 ketene, 307, 308,439,507,522,819,821,822, isonitrosoketone, 1634 824,1026,1064,1221,1222,1371,1372, isonoragathic acid, 493 1561,1683,1821,1922,1991,1996,2495, isooxazole, 1668 2496,2497,2636,2637,2638,3073,3075 isopentane, 851, 2038 ketenimine, 819, 822, 824, 1968 isophosphamide, 2647 keteniminium cation, 822 isopinocampheol, 119 keteniminium ion, 1221 isoporphine, 2429 keteniminium Pictet-Spengler cyclization, isoprene, 1693,2675 2211 SUBJECT INDEX 3647

, 1481, ketirrtine, 66,273, 274, 804,841,843,1027, lecithin, 2818, 2819 2738, 1496,1988,1989,1990,2727,2770,2771 Lemieux-Johnson reagent, 1734 ketine, 1302 lepidine, 25, 26, 1640,2890 ketoacetanilide, 692 Leuckart-Wallach alkylation, 1738 ketoarnine, 74, 1403 Leuckart-Wallach reaction, 1738 ketoepoxide, 2994 Levinstein mustard gas, 1747 )44, ketoirrtinatocobalt complexes, 1383 levulinic acid, 1085, 1371 Z57, ketoketene, 822 lignite, 337 ketone thioserrticarbazone, 1330 limonene, 643 ketonic acid, 1388 Lindlar catalyst, 1758, 1759, 1760 ketonization, 553 linoleic acid, 2864 ketopinic acid, 1351 linseed oil, 3183 ketoxime, 288, 1434, 2017, 2020, 2260, 2552, liquefaction, 337 2553,2793,2794 List-Barbas-Mannich reaction, 1820 ketyl radical, 493, 1245, 1273 alkylphosphonamide, 730 ketylidene, 2385 lithium thiophenoxide, 422 Kindler modification, 3018, 3020 Loftfield mechanism, 1026 Kindler variation, 3018 loganin, 2969 kinetic preference for reaction at the 3-position Lombardo reagent, 1767 but thermodynarrtic preference for formation Lombardo-Oshima reagent, 1767 of the C-I adduct (K3Tl), 1884 Lombardo's reagent, 1767 Kishner-Leonard elimination, 3085 longicyclene, 2931 Knoevenagel condensation polymerization, longifolene, 2931 1621 lophine, 2293 Knoevenagel polycondensation, 1621 lophocerine, 442 kojic acid, 374 LOST, 1747 Kolbe electrolysis, 1443,1444,1656 lowest unoccupied molecular orbital, 886 Kostanecki-Robinson acetylation, 1679 Luche reagent, 1782 Kostanecki-Robinson phenylacetylation, 1679 LUMO, 606, 683, 821, 886, 887, 2271 Kozikowski modification, 2530 Iyxose, 2446, 3056 Krohnke salt, 1697 m-chloroperoxybenzoic acid, 150 L-malic acid, 2937, 2938 m-hydroxybenzoic acid, 1041 lactol, 1055, 1734, 1809, 2718, 3032 m-naphthoxazine,374 , 58, 150, 151,210,307,355,356,402, m-thiazine, 107 426,468,529,820,1015,1055,1056,1155, m-trifluoromethylphenol, 1666 1279, 1521, 1522, 1613, 1683, 1706, 1707, m-xylidine, 1418 1722,1782,1923,2303,2504,2602,2718, macrolactone, 1601, 1602, 1603, 1760,2750, :41,2221, 2937,2938,2957,2989,3032,3111 3109 lactonization, 525, 1615 macrolide, 47, 1021, 1485,3109,3110 lactosamine, 1403 magic acid, 1877 996 laevulinic acid, 1072 maitotoxine, 2680 821,822, lampblack, 183 makaluvamine C, 571 ,1372, lanthanide triflate, 1143 malachite green, 1041 5,2495, laudanine, 410 maleic anhydride, 1617, 2368, 2926, 2927, 3,3075 laudanosine, 410 2928,2929 laulimalide, 2583 maleimide, 1617 lauroin, 16 malonate, 1307, 1570, 1621, 1622, 1688, 1811, Lawesson's reagent, 1166, 1724 1813,1901,1902,1903,1922,1923,1996, tion, lead tetraacetate, 403,761,762,763, 1288, 2165,2188,2234,2813,3074,3130 1647,2673 malonodinitrile, 834 3648 SUBJECT INDEX mandelate, 1983 metalation, 2346, 2803, 3050, 3102 mandelic acid, 1816, 1817, 1818,2022, metalative Reppe reaction, 2346 2024 metalJa di-IT-methanerearrangement, 910 mandelonitrile, 1078, 1818 metallahexatriene, 934 manganese dioxide, 173, 174, 175, 722, 1504, metallazetidine, 2754 1677 metalJo-carbene complex, 57 manganese, 202, 935, 1534, 1570, 1646, 1778, metallocene dihalide, 3145 1779,1780,1893,2077,2389 metallocycle, 2346 Mannich base, 1820 metalloenzyme, 2484 mannitol, 761, 1872,2362 metalJooxetane, 2754 manzamine, 2680 metathesis, 57, 58, 59, 582, 1647,2030,2347, Markovnikov addition, 1833 2753 Markownikoff addition, 1833 methanephosphonate,2647 Martin's sulfurane, 1841, 1843 methanesulfonamide, 947, 948 MAS, 389 methanesulfonic acid, 425, 572, 2256, 2504, McCormack adduct, 1849 2931 McCormack cycloadduct, 1849 methiodide salt, 1714 McL..fferty + I rearrangement, 1857 methional, 2702 McLafferty rearrangement with charged methone, 302 olefinic product, 1856 methoxypyridine, 1714, 3172 McLean-van Slyke method, 2860 methyl acetoacetate, 149 McMurry reagent, 1860 methyl chlorosulfinate, 367, 368 mCPBA epoxidation, 2270, 2271 methyl crotonate, 2043, 2147 Meerwein-Ponndorf-Oppenauer-Verley methyl f1uoroacetate, 1291 reduction, 1871 methyl hyodesoxycholate, 1942 Meerwein-Ponndorf-Verley-Oppenauer methyllinoleate, 493 reaction, 1871 methyl p-isopropylbenzoate, 15 Meerwein's reagent, 1877 methyl sulfate, 66, 642, 1338, 1339, 1526, Meerwein's salt, 1877 1529, 3027 melanoidin, 1795 methyl sulfite, 366, 368 meldrum's acid, 693, 694, 1621 methylacrylonitrile, 821 mellanoidin. 1404 methylation, 429, 726, 1009, 1010, 1451, 1526, menthene, 643, 699 1527 mercuration, 1475 methylcarbinol, 136, 1750, 1751 mercuric cyanide, 1367 methyJcholanthrene, 429 mercuric triflate, 1918 methylenecyclobutane, 821 mercury(II) trifluoromethanesulfonate, 1918 methylenecyclobutenone, 1014, 1015 Merrified resin, 1905 methylhydrazine, 2084 Merrifield solid-phase peptide synthesis methyloxosulfonium ylide, 713 (SPPS), 1905 methylpseudoephedrine, 2975 mesitaldehyde, 1202, 1247, 2615 methylpyrrolidone, 1292, 1905,2794 mesitoyl chloride, 1274 Michael acceptor, 1922, 1923, 1996 mesitylacetic acid, 1657 Michael adduct, 695, 1922 mesitylene, 132, 1006, 1531,3145 Michael donor, 1922 mesitylmagnesium bromide. 6 Michael-Stork (enamine) addition, 2695 meso-endoperoxide, 1677 Michaelis-Arbuzov product, 2169 mesyl , 2322, 2324 Michaelis-Becker reaction, 1931 meta director, 776 Milas reagent, 1948 metacyclophane, 88 I, 3I86 Mitsunobu cyclization, 1955 ammonia solution, 389 modhephen, 2969 metal-catalyzed acetylene trimerization, 2345 Moffatt reagent, 1962 metal-promoted Fries rearrangement, 1144 molecular weight distribution (MWD), 3147 SUBJECT INDEX 3649

mo1ozonide, 765 N-tosy1azetidine,2399 montmorillonite K-IO, 568, 569, 1046, 2049, N-viny1pyrro1e, 2793 o 2050,2152 N,N'-diacetylchitobiose, 1765 montmorillonite KSF-clay, 2107 N,N'-diaryhydrazine, 320 montmorillonite, 151, 1132,2107,2152 N,N'-diisopropylcarbodiimide, 165, 1487 morphinan, 2219 nation membrane, 1144 morpho1ine, 833, 1215,2364,2695,2696, Nation-H, 1127,2152 2697,2831,2957,3018,3019,3020, nanotube, 389, 2519,3086, 3095 3022 naphtha1amine, 2844 Morrison-Brunn-Huisgen intermediate, 1955 , 132, 134,317,392,553,554,646, 2347, Mosher ester, 1983, 1985 647,776, 1055, 1227, 1228, 1342, 1347, Mosher's acid, 1983, 1984, 1985 1399,1400,1861,1863,1884,2005,2185, Mosher's reagent, 1983 2388,2389,2454,2455,2544,2817,3082, Mozingo condition, 2789 3096,3190 504, Mukaiyama-Michae1 addition, 1922, 1996 naphtha1othiophene, 820 multicomponent condensation, 2831 naphthol, 375, 376, 553, 554, 977, 1228,2329, mu1ticomponent reaction (MCR), 107,379, 2330,2844 557,1457,2710,2831 naphthy1amine, 507, 549, 553, 554, 923, 927, multistep synthesis, 25, 2341, 2789 1415,2246 munchnone, 1504, 1505 naphthy1hydrazine, 551, 1558 muscone, 438 naphthy1hydrazone, 551 mustard gas, 1747, 1749 naphthyridine, 631, 693, 1139, 1670 myo-inosito1, 1051 NaY-zeolite, 1351 myristic acid, 2864 neocarzinostatin, 2003 neopentyl chloride, 1647 N-acetonaphtha1ide, 2092 neutral palladium complex, 1350 N-acy1-oxazo1idone, 1021 Nicholas cyclization, 2049 t6, N-acyliminium Pictet-Speng1er condensation, Nicholas-Schreiber reaction, 2049 2210 acetylacetone, 1777 N-acyliminium Pictet-Speng1er reaction, 2210, NiCI2,68,204,431, 1274, 1930,2077,2079 2211 nicotina1dehyde, 1078 I, 1526, N-a1ky1aniline, 924 nicotinamide, 3173, 3174 N-ally1pyrro1idine, 309 nicotine, 3173, 3174 N-ary1a1dimine, 1234 nine-component reaction, 2830 N-benzoy1piperidine, 2900 ninhydrin, 1831,2701,2702,2860,3034, N-bromophtha1imide, 3067 3176 n-butyra1dehyde, 1728 niphendipine, 1622 N-ch1orosuccinamide, 1194 nitrendipine, 1622 N-g1ycoside, 74, 2915 nitrene, 780, 781,1376,1434,1772,2018, N-ha1oamine, 1464 2674,2730 N-iodosuccinimide, 1521 nitrile, 245, 272, 288, 316,411,424,425,426, N-methoxy1-N-methyl amide, 2956 501,512,536,683,841,994,1076,1260, N-methy1 pheny1ethylsu1fonamide, 1466 1261,1273,1430,1491,1496,1661,1706, N-methy1pyridone, 1714 1778,1913,1935,1972,1988,2017,2029, N-phenacy1phthalimide, 1185 2237,2238,2251,2252,2302,2399,2406, N-pheny1aminothiocarbony1eremomycin, 957 2425,2471,2540,2548,2552,2563,2651, N-pheny1oxazolidine, 2363 2659,2660,2661,2678,2710,2711,2713, N-pheny1phthalimidine, 1083 2718,2726,2727,2766,2767,2770,2771, N-pheny1su1fony1pyrro1e, 1266 2773,2852,2901,2904,2905,2911,3000, N-succinimide chloride, 726 3119,3120,3130 N-sulfony1-Pictet-Speng1er reaction, 2211 nitri1iumcation, 289 3147 N-su1fonylcarbazo1e, 2201 nitri1otriacetate, 1041 3650 SUBJECT INDEX nitro-Mannich reaction, 1383, 1820 o-methoxphenol, 2267 nitro-Mannich reaction, 1383, 1820 o-methylbenzophenone, 982 nitroalkane,48, 1383, 1922,2025,2026,2586, O-methylvalerolactim, 1715 2587,2651,2759,2868 o-nitro-cinnarnic acid, 140 nitroarene, 228 o-nitroaniline, 695. 1395 nitroaromatic, 1542, 1543, 1895 o-nitrophenylacetic acid, 144 nitrobenzofuroxan, 482, 483. 1885 o-nitrosophenol. 263, 264, 265 nitrodecarboxylation, 1512 o-nitrotoluene, 258, 2341,2342.2807 nitroinosine, 89 o-oxyarylketone, 220 nitromethane, 475, 669,671,1128,1131,1369, o-phenanthroline, 1147 1385,1390,1884,1893,2025,2777,2823 o-phenylenediamine, 331, 1569, 2084, 2199, nitrone, 515, 516, 517, 964,1083 2387 nitroparaffin, 2586 o-phthalaldehyde, 1426 nitrophenol, 263, 353,1314,1821,1893,2244, o-tolualdehyde, 2178, 2659 2383,2808,3081,3082,3168,3169,3170 o-toluic acid, 898 nitrosation, 263, 264, 2789 o-vinylacetanilide, 1360 nitrosoamide, 1132 o-xylene, 897, 1377 nitrosobenzene, 1083 octahydroanthrance. 1531 nitrosomethylurea, 2149 octahydrophenanthrene, 216, 217, 218, 455, nitrotoluene, 186, 187,258,1314,1893,2341, 457, 1531 2342,2807.2870 octaphenanthrene, 218 nitroxyl, 81. 2368 ODPM rearrangement. 910 NOBIN,553 oestrogen, 2330 nocardicin, 2636 Oglialoro modification. 2161 nonasulfide, 1747 Ohira's reagent, 2560 nonenzymatic browning reaction, 1795 olefin disproportionation, 57 nonionic surfactant, 1032, 1033 oleoyl chloride, 1289 norbornadiene, 820, 2364, 2367, 2368 oleum, 459, 461. 2808 norbornene, 372,2030, 2131,2367, 2368,2753 oligosaccharide, 1338, 1593, 1595,3036 norcaradiene, 562 one-pot Smiles rearrangement, 2611 Norrish type I photosensitizer, 2062 optical antipode, 375 norsteriod, 1027 Orange II, 1041 Noyori catalyst, 2072 organosilane, 837, 1430,3097,3145 Noyori/lkariya catalyst, 2072 organostannane, 2677, 2678, 2679, 3097 Nozak-Hiyama allylation, 2076 orientin, 2983, 2984 Nozaki-Hayashe methylenation, 1767 Oriyama's diamine, 2799 Nozaki-Hiyarna-Kishi cyclization, 2076 ornithuric acid, 2536 nucleofuge, 1279, 2931 ortho-nitrobenzenesulfonation. 1159 nupharidine, 2251 ortho/para director, 776 nylon 6,288 orthoester, 771, 1217. 1561, 1562, 1722, 241 1, 2660 o-alkenylphenylisocyanide, 1164 orthoformate, 448, 450, 694, 907, 949, 950, o-amino thiophenol, 1395, 1396 2720 o-aminobenzenethiol, 2198 orthophosphoric acid, 870, 2195, 2256 o-aminophenylthioglycolic acid, 1395 orthosilicate, 1131 o-aminostyrene, 1165, 1358,3008 osazone, 1083, 1084,1085,1086,2084,2085 o-benzoylbenzoic acid, 1347 osmium tetraoxide, 1734, 1735 o-dimethoxybenzene, 2267 osmium tetroxide, 1735, 1948, 1950, 3090 o-ethynylaniline,616 Ostwald process, 81 O-glycoside, 1367, 1650, 1651.3045 oxa-di-Jr-methane rearrangement, 910 o-hydroxyacetophenone, 1680 oxa-Pictet-Spengler cyclization, 2210 o-iodoaniline, 1717, 1718. 1719 oxa-Pictet-Spengler reaction, 2210 SUBJECT INDEX 3651

oxacarbenium ion, 1594 p-bromobenzenesulfonamide, 302 oxadiazinone, 1021, 1023 p-chloranil, 2431,2432 oxadiazole,484, 1061, 1883 p-chlorophenol, 469 oxalate, 173,461,478,480,952, 1131,2342, p-dimethy1aminobenzenediazonium 2343,2938 tetrafluoroborate, 973 oxaphosphetane, 3031, 3034, 3035 p-hydroxybenzoic acid, 1041 oxathiadiazole, 2774, 2775 p-nitrobenzenesulfonylhydrazine, 1005, oxathiaphosphate, 2648 1006 oxathiaphospholane, 2648, 2650 p-nitrohippuric acid, 2536 oxazaborolidine, 709, 734, 735 p-nitroperbenzoic acid, 770 ,2199, oxazaborolidinone, 1997 p-nitrosotoluene, 2246 oxaziridine, 304 p-phenylazobenzenesulfonyl chloride, 1419 oxazole, 855, 1076, 1668, 1670,2293,2294, p-quinindane, 2188 2410,2529,2531,2656,2657,2658 p-quinone, 263, 2147 oxazole[3,2-a] pyridinium, 511, 512 p-tolualdehyde,450, 1204, 1623 oxazolidinone, 531, 1023, 1076, 1222,2638 p-toluenesulfonanilide, 1420,2363 oxazo1idone, 780, 781,1021, 1023 p-toluenesulfony1hydrazide, 198, 239 oxazoline, 545, 548,2049,2206,2843 p-toluenesulfonylhydrazine, 1005, 1006 8,455, oxazolone, 353, 355,997 p-to1uenesulfony1hydrazone, 195, 196,2563 oxetane,819,1841,2126,2127 p-toluidine, 1250,2246 oxidative decarboxylation, 1646, 1647,2701, palladacycIe, 1718,2630,2734,2737 2702 palladium, 145,337,443,471,472,575,576, oxidative Nef reaction, 2026 577,620,796,1350,1351,1352,1354, oxime, 93, 245, 247,263, 288, 289,290, 512, 1358,1359,1430, 1718, 1754, 1755, 1758, i no, Ill2, 1360, 1434, 1634, 1636, 1637, 1759,2029,2132,2352,2421,2462,2463, 1857,1860,1945,2017,2019,2260,2552, 2628,2630,2677,2678,2733,2734,2735, 2553,2630,2676,2759,3056,3129 2736,2737,2798,2799,2812,2813,2843, oximino ketone, 1302 2920,2921,2922 1036 oximinoketone, 1112 palmitic acid, 1373,2864 oximinosulfonate,2675 palygorskite, 151 oxindole, 145, 1194, 1416,1621,1840 papaverine, 410, 548 oxirene,3075 paraconic acid ester, 2687 oxo-Michael addition, 1922 paraformaldehyde, 134,430,431,531,1590, 3097 oxoamide, 1170, ll71, ll73 3183,3192 oxocarbenium, 1046, 1088,2173 PBr), 68, 673, 2902 oxomalonic acid, 1838 pectenine, 410 oxomanganese salen, 1534,2484 pellagrin, 3174 oxone, 1535, 1735, 1736,2590,2591,2592, penicillin, 350, 1979,2636 2593 pentachlorophenol, 1041 722,2411, oxosulfonium salt, 715 pentaerythritol, 2362 oxybenzylalcohol, 160 pentaethylbenzene, 181, 1530 ~9, 950, oxybenzylmethylen-glycolanhydride, 161 pentafluorobenzene, 1131, 1132 oxyethylation, 3136 pentafluorobenzenesulfonate, 1131 ~56 oxyketene, 308, 822 pentalenene, 2969 oxynitration, 3081, 3082 pentamethy1 , 134 084,2085 ozaphyrin, 2429 , 1530 ozonide, 765,1438,2303 pentasil zeolite, 1144 J,309O ozonolysis, 765, 766, 1834 peracetic acid, 1103 perbenzoic acid, 1426,2270,2271 10 p-anisa1dehyde, 603 pericyclic reaction, 2011, 2373, 2637, 2882 10 p-anisidine, 25, 1307,2772 perimidine, 2198 p-benzoquinone, 1041, 1361 peristylane, 2969 3652 SUBJECT INDEX

Perkin-Oglialoro condensation, 2161 phospha-Michael addition, 1922 Perkin-Oglialoro reaction, 2161 phospha-Stevens rearrangement, 2668 Perkow product, 2169 phospha-Wittig reaction, 3031, 3032 pennanganate, 1477,2199,2586,2860,2861 phosphacymantrene, 2873 peroxodisulfate, 977 phosphanorbornene,2882 peroxyacetic acid, 150,452,454 phosphinamidate, 2648 peroxybenzoic acid, 150,452 phosphinidene, 2882 peroxydisulfate, 498,977,979 phospholene oxide, 1849, 1850, 1851 perphthalic acid, 1787 phospholene, 1849, 1850, 1851,2882 persistent radical, 1239 phosphonamidate, 1723 petaline, 410 phosphonamide, 730, 731, 1484, 1485 Petasis-Tebbe reagent, 2753 phosphonite, 2642 Pfaltz ligand, 1351 phosphonium ylide, 1484,2963,3031,3035 Pfitzner-Moffatt reagent, 2193 phosphonylimine, 1821 phenanthraquinone, 1227 phosphoramidite, 2649, 2799, 3164 , 215,216, 218,455,457,478, phosphoramidous acid, 3164 501,901, 1227, 1342,2823 phosphoroselenoate, 2647 phenanthridine, 1971, 1972, 1973,2335,2674 phosphorose!enothioate, 2647 phenanthridone, 1972 phosphorothioate, 2647 phenanthroline, 685, 1147, 1572,2335,2604, phosphorous pentoxide, 1347 2605 phosphorus oxychloride, 547, 673, 675, 1364, phenazine N-oxide, 3060, 3061 2410 phenazine, 304,2839, 3060, 3061 photo-anilide rearrangement, 1144 phenetole, 2267 photo-Arbuzov rearrangement, 1929, 1930 phenolphthalein, 1699, 1701, 3165 photo-Fries reaction, 1144,2200 phenoxide, 388,1570,2329,2330,2348,2847, photo-Fries Rearrangement, 1144, 1145,2200, 3027,3188 2201 phenyl glycoside, 1363 photo-Fritsch-Buttenberg-Wiechell phenyl isothiocyanate, 954 rearrangement, 1152 phenyl ,8-naphtholaminomethane, 374 photo-Nazarov cyclization, 2011 phenylacetaldehyde, 635, 637, 2661, 2702 photo-Smiles rearrangement, 2610 phenylacetamide, 2303, 3019 photo-Stevens rearrangement, 2668 phenylacetonitrile, 974, 2661 photo-Wagner-Meerwein rearrangement, 2930 phenylacetylene, 101,2471,2631,3019 photo-Wallach rearrangement, 2942 phenylalanine, 355,2210,2702,2703,2704 photo-Wolff reaction, 3073 phenylazide,948 photo-Wolff rearrangement, 3073 phenylazoimide, 947 photoacid, 2202 phenylboronic acid, 711 photoanilide rearrangement, 2201 phenylcinnamonitrile, 1621 photochemical pinacol rearrangement, 2228 phenylglycocollorthocarboxylic acid, 1399 photochemical Smiles rearrangement, 2609 phenylglyoxal, 2243 photochemical Wagner-Meerwein phenylhydrazine, 549, 551, 1072, 1080, 1083, rearrangement, 2930 1086,1191,1390,1558,1560,2084,2085 photochemical Wohl degradation, 3056 phenylhydrazone, 1083, 1085, 1390, 1845 photochemical Wolff rearrangement, 3073 phenylisonitrile, 1164, 1458 photoinduced Wolff rearrangement, 3073 phenylsulfamate, 2201 photolytic Wolff rearrangement, 3073 phenylsulfinic acid, 1217, 1219,1422 photooxidation, 1440 phenylthiohydantoin, 954 photosensitizer, 1464,2062 phenyltriethoxysilane, 3146 phthalazine, 2335 phloroglucinol,944, 1146, 1498, 1903,2188 phthalazone, 2439, 2441 phosgene, 359, 1466,2243,2410,2873 phthalic anhydride, 43, 1227, 1228 phosophonothiate, 730 phthalimide, 1176, 1399,1400,1956,2399 SUBJECT INDEX 3653

phyllanthocin, 1021 propiona1dehyde, 986, 2852 8 picoline, 892, 894, 895, 994, 995, 2482, 2998, propionamidine, 2241 3174 propiophenone,598, 1750,2220 picolinic acid, 1314 , 1710,2014 picrotoxin, 3130 protein, 350,483,954, 1403, 1884, 1905,2488, pimelic acid, 433 2489,3165 pinacolborane, 536, 3012 protiodesilylation, 529 pinacolone, 1750,2227,2228,2379 protiodetritiation, 2823 piperazine, 1252, 1264,2303 pseudo-phthalazone, 2439 piperidine, 77, 147,374, 1187, 1464, 1622, pseudocoarctate rearrangement, 2909 5 1623, 1623, 1624, 1675, 1905, 1906, 1923, pseudohalide, 575 2219,2695,2696,2888,3019 pseudopelletierine, 2358 1,3035 piperidone, 2182, 2183 ptilomycalin A, 380 piperitone, 2994 pumiliotoxin B, 2680 piperonal, 723, 843, 2491, 2529, 3083 Pummerer cyc1ization, 2284 pivalaldehyde, 1853 purine, 631, 1409,2335,2789,2915,2916 pivaldehyde, 2437 pyrazine, 631, 1264, 1302, 1303, 1304, 1447, pivalic acid, 1642 1669,2335,2373 Poisson distribution, 3134 pyrazole, 1631,2147,2218,2806 poly-neopentylglycine, 1584 pyrazoline, 1617, 1618,2147,2217 75,1364, polyacetylene, 959 pyrazolone, 892, 893, 894, 1631 polyalanine, 1583 , 776 polyalkylbenzene, 128, 134 pyridazine, 606, 2335, 2369 1930 polyalkyne, 1151, 1152 pyridine, 3,25,65,66,89, 147, 170, 192,220, polyene alcohol, 173 246,360,364,399,483,512,547,604,616, 45,2200, polyene, 820, 1609,2680 622,631,646,736,739,832,846,847,892, polyester, 1014 957,960,967,993,1036,1174,1279,1294, poly ketene, 437 1390, 1668, 1670, 1695, 1703, 1864, 1897, polyleucine, 1583, 1584 2145,2161,2239,2267,2287,2291,2336, polymer po1ydipersity index, 3147 2412,2476,2535,2536,2565,2568,2651, polyoxazole, 624 2753,2849,2998,3000,3001,3019,3109, polyphosphoric acid, 34, 688, 689, 998, 1342, 2121,3130,3139,3173 ent, 2930 1917,1973,2151,2249,2410,2553,2838, pyridinium ylide, 1695, 1696 3179 pyridone, 803,2348 polyquinane, 2968, 2969 pyridylcarbinol, 1314, 1315 polyquinene, 2969, 2970 pyrimidine, 631,1408,1410,1669,2233,2234, po1ysilane, 3097 2329,2335,2789,2916 polysulfide, 1747,3018,3021 pyrollidine, 1027, 1028 t,2228 Pomeranz-Fritsch-Bobbitt cyc1ization, 2257 pyrolysis, 7, 30, 31, 43, 366, 368, 369, 642, :,2609 porphine, 2429 697,780,982,1013,1014,1015,1016, porphyrin, 254,255, 562, 1635,2346,2429, 1256, 1379, 1451, 1460, 1461, 1462, 1699, 2431,2432,2873 1713,1829,2480,2533,2548,2730 56 cyanide, 333, 557, 722, 1284, 1662, pyrone, 147, 149, 1679, 1812, 1901,1903 3073 2710,2911,2912,3120 pyrrole Weinreb amide, 2956 \073 potassium superoxide, 19 pyrro1e,147,258,259,390,570,646,647,665, 3 potassium trioxalatocobaltiate, 952 666,1036,1171,1173,1256,1326,1427, Prileschajew reagent, 2270 1504,1634,1635,2107,2108,2217,2219, Prins- Kriewitz cyc1ization, 1692 2429,2431,2794 proazaphosphatrane, 2308, 2309, 2678 pyrrolidine,968, 1138, 1252, 1464, 1504, propargylic alcohol, 101,2049,2358,2506 1821,2364,2695,2696,2888,2890 propargylsilane, 837 pyrrolidone, 1292, 2363 ,2399 propellane, 2970 pyrroline, 837, 1266, 2529 3654 SUBJECT INDEX pyrrolopyrimidine, 907 Reppe chemistry, 2352 pyruvaldehyde. 2293, 2701 Reppe hydroforrnylation, 2353 pyruvic acid, 557, 921, 922, 923, 1390, 1845, Reppe reaction, 2346, 2348, 2352, 2353, 2358 1846 resorcarene, 3186 resorcinol, 220, 303, 2036, 2153, 3130, 3179, quadricyclane, 820 3186 quadrone, 2969 reticulatacin, 1609 quasi-Favorskii rearrangement. 1026 retro Patemo-Biichi reaction, 2127 quinaldic acid, 1284, 2336 retro-Brook rearrangement, 529 quinaldinic acid, 1314 retro-Reforrnatsky fragmentation, 2314 quinamine, 90 I retro-Wittig reaction, 3032, 3034 quinazoline, 1264,2055,2335 retro-Wolff rearrangement, 3074 quinine, 25, 26, 952, 1923, 1925,2570,2574, retrojusticidin B, 1057 2638.2975,2976 reverse aza- Payne rearrangement, 2140 quinoline Reissert compound, 2335 reverse Brook rearrangement, 529 quinoline, 315, 599, 600, 646, 688, 689, 690, reverse thia-Payne rearrangement, 2140 894,895,924,925,995,1137,1138.1139, rhamnose, 1615 1164,1165,1167,1269,1284,1314,1570, rhodanine, 1260, 1261 1622,1751,1758,2188,2389,2335,2336, rhodium, 68, 81, 562,1351,1516,1517,2072, 2337,2341,2421,2422,2467,2603,2604, 2132,2799,2881,3073,3076 2605,3174 ricinoleic acid, 2373 quinolinic acid, 921 Rieke metal, 2388, 2389 quinolinol, 374, 375 Rieke Mg, 2388 quinolone, 892, 894, 1069 Rieke Ni, 2388 quinolyl-4-a-piperidylcarbinol, 25 Rieke zinc, 2029 quinone, 341, 342, 460, 619, 793, 1055. 1422, Rieke Zn, 2388 1477,1584,1967,2007,2042,2043,2129, ring-closing metathesis, 57 2431,2463,2707,2762,3169 ring-opening metathesis polymerization, 2030 quinoneimide, 838 Rink amid resin, 1977 quinonoidation, 1238 robustaflavone, 2983 quinoxaline, 303, 1055, 1264,2084,2085,2087 ROMP, 57, 58 quinuclidine, 275, 2570 rose Bengal, 1677 rotaxane,2814 radical Brook rearrangement, 529 Roush crotyl boronate reagent, 2435 radical hydrogen abstraction, 1438 Roush crotylborane, 2435 radical-molecule reaction kinetic, 1239 rule of five, 821, 822 Raney cobalt, 2304 ruthenium tetroxide, 211 Raschig ring, 1015, 2362 ReM, 57 S-LOST, 1747 red phosphorus, 1373 safrole oxide, 2491 reducing sugar, 29, 30, 75, 1795,2718 salen, 1534, 1535, 1923,2077, 2222, 2272, reductive alkylidenation, 1170 2484,2783,2799 reductive amination, 766, 1009, 1264, 1737, salicyclic acid, 1664 2303 salicylaldehyde, 1622,2330 Reformatsky reagent, 424, 425,1235,2314, salicylic acid, 1664 2315,2316 salicylihalamide, 1021 refractive index, 119, 120, 368, 2482 saligenin, 160 Reissert compound, 1287, 2335, 2336, 2337 saliretin, 160 Reissert condensation, 2341 Salkowski-van Slyke method, 2860 Reissert synthesis, 2341 salox,2849 reluctant Norrish type I reaction, 2062 salsolidine, 442 REM resin, 1453 salsoline, 410, 442 SUBJECT INDEX 3655

samarium iodide, 1279, 1280, 1576 Sharpless rule, 2574 Sandmeyer reagent, 2471 shellac substitute, 160 ,2358 sanglifehrin A, 2680 Shiori reagent, 781 santonin, 900 sialic acid, 2499 3179, saponification, 43, 370, 371,439,2820 sila-Pummerer rearrangement, 2285 sapphyrin, 2429 sila-Sonogashira reaction, 2628 Sarett's reagent, 2476 silane, 529, 1103, 1173, 1310, 1351, 1430, sativene, 2931 1821,2176,2276,3146,3147,3150 saxitoxin, 424, 426 silanol, 532, 1430 Saytzeff product, 1460, 2480 silicate, 1131, 1430 Saytzeff regiospecificity, 2480 silicon Pummerer rearrangement, 2285 Schiff base, 441, 692,863,922,964, 1235, siloxy-[2,3] Wittig rearrangement, 3049 1314,1403,1723,1821,1923,2197,2221, siloxyacetylene, 1684 2484,2486,2673,2711,2770,2799 silver carbonate, 1055, 2450, 245 I, 2938 Schlenk equilibrium, 1274 silver cyclobutanecarboxylate, 404 Schlittler-Miiller modification, 2257 silver oxide, 722, 1180, 1526, 1529,2701, Schmiere, 160 2937,2989,3056 Schollkopf his-lactim ether chiral auxiliary, silver perchlorate, 398 ',2072, 2523 silybin, 1369 Schollkopf bis-Iactim ether, 2523,2524 silyl-Hilbert-Johnson synthesis, 1408 Schollkopf chiral auxiliary, 2523 silyl-Prins reaction, 2276 Schollkopf reagent, 2523 silyl-Stobbe condensation, 2687 Schollkopf''s observation, 2523 silyloxydiene, 1821 Schollkopf''s rule, 2523 Simmons-Smith reagent, 2594 Schotten-Baumann benzoylation, 2536 single-electron-transfer, 202, 1172, 1273, 1866, Schulz-Flory distribution, 3136 1867, Schwesinger base, 2965, 3032, 3033, 3035 singlet, 820, 821, 823,910, 1144, 1376, 1438, 1,2030 scutegalin B, 2477 1535,1675,2062,2067,2068,2126,2127, sedoheptulose, 1365 2200,2201,2368,2515,3075 selectfluor, 1512, 1513 skatole, 142 selenide, 683, 2303, 2550 Skraup-Doebner-von Miller quinoline selenium dioxide, 2395 synthesis, 924 seleno Pummerer reaction, 2286 amalgam, 29, 30, 31, 32,989,1260, selenophene, 1427 1474, 1576, 1613 semi-Michael addition, 1558 sodium borohydride, 1782, 1784, 1913, 1916 semi-pinacol rearrangement, 2228 sodium hypochlorite, 1111, 1399, 1535,2701, semibullvalene, 2969 2946,3004 semicarbazide hydrochloride, 439, 2627 sodium hypophosphite, 179, 2303 semicarbazide, 305, 439, 971, 2084, 2627 sodium metaperiodate, 211, 1428 semicarbazone, 440, 1330, 1845,2627, sodium percarbonate, 1583, 1584 272, 2770,3084 soft Nef reaction, 2026 semicorrin, 1003 solamin, 1609 serine, 1213,2656,3106 solandelactone, 3109 serotonin, 557, 571 solid-phase support synthesis, 954, 1070 serratezomine A, 2253 solvolysis, 1650,2276,2931 serratinine, 2253 sorbitol, 2362 SET, 202, 1172, 1273, 2221 sparteine, 1024, 1830,2782,3052 Seyferth reagent, 2559 sphingosine, 1187 Seyferth-Gilbert diazophosphonate reagent, spin-orbit coupling, 2127 2559 spirane, 455, 2989 Seyferth-Gilbert reagent, 2559, 2560 spiroepoxide, 1967 Sharpless kinetic resolution (SKR), 2581 SPSS,954 3656 SUBJECT INDEX squalene, 1561, 1562 sulfonation, 478, 549,1418, 1531,2244,2708, squaric acid, 822 2822,2823,3186 stable radical, 1239, 1866 sulfone, 369, 683, 762,841,974,1144,1422, stanna-Brook rearrangement, 530 1426,1475,1577,1621,1821,2298,2299, stannane, 1238, 1351, 2680, 3052 2303,2610,2611,2735,2803,2804,2805, stannyl-Brook rearrangement, 530 2806,2823 Staudinger-aza-Wittig reaction, 3032 sulfonylhydrazine, 1005 Staudinger/czc-Wittig reaction, 3032 sulfonylquinol, 1422 staurane, 2969 sulfoxide, 841,1595,1952,1979.1980,2285, stearolic acid, 2864 2286,2303,3032 stearylsulfonic acid, 2817 sulfoximine, 841, 2806 stereoregularity, 3146 sulfur monochloride, 1395, 1397, 1747 stereotriad, 2783 sulfur mustard, 1747 steric acceleration due to the hindered rotation sulfuration, 1722 (SAHR), 627, 2046 sulfurylaniline,781 steroid, 210, 245, 246, 289,434,877,878,897, super-conjugation, 69

901,1027,1028,1155,1845,1940,1941, supercritical CO2 , I J32, 1360,2202,2229, 2007,2193,2317,2405,2556,2557,2988, 2406,2576,2922 2989,3158,3159 suprafacial-suprafacial interaction, 887 stilbene, 820, 1535, 1538, 1622, 1736, 1860, Suzuki polycondensation, 2733 1948,2265,2592 Swarts mixture, 2744 Still-Wittig [2,3]-sigmatropic rearrangement, Swarts reagent, 2744 3049 Swarts rule, 2744 Stobbe acid ester, 2686 Swem-Moffatt reagent, 1962 Stobbe product, 2686 swinholide A, 1218 Stork acylation, 2695 SWNT,389 Stork addition, 2695 sydnone, 164 Stork enamine addition, 2695 sym-tetrachloroethane, 222, 403 Stork-lung vinylsilane reagent, 3004 sym-triazine, 2241, 2242 Strecker aldehyde, 2701 syndiotacticity, 3146 Strecker-Bucherer reaction, 2710 synthesis gas, 1098, 1516 Strecker-Bucherer synthesis, 27 10 strychnine, 2680 r-butyl hydroperoxide, 1950, 2977 suberoin, 1319 tacticity, 3146, 3147 succindialdehyde, 2414, 2415 Takai-Nozaki methylenation, 1767 succinic anhydride, 434, 1342,2506 Takai-Nozaki olefination, 2748 sulfamic acid, 1138, 2151 Takai-Utimoto reagent, 2748 sulfaminic acid, 2244 takatonine, 410 sulfanilamide, 224, 3065 tandem oxidation process, 723 sulfenyl halide, 3163, 3164, 3165 tartaraldehyde, 2414 sulfimide, 1593 tartaric acid, 1829,2966 sulfinic acid, 1422,2373,2789,2803 tautomycin, 1021 sulfinil glycoside, 1593 taxol, 624, 625 sulfinyl Pictet-Spengler reaction, 2211 Tebbe reagent, 1172, 2081, 2753, 2754, 2755 sulfite. 152,366.368,369,551,553,554,846, tedanolide, 1021 1080, 1131, 1929,2160,2244,2707,2708, temperature-programmed desorption (TPD), 2709,2911 3145 sulfochlorination, 2311 TentaGel resin, 1140 sulfolane, 97, 513, 590 terephthalaldehyde biscyanohydrin, 333 sulfonamide, 591, 654,1159,1418,1821, terephthaldialdehyde, 1622 2363,2568,2569 terephthalic acid, 1381 sulfonanilide, 1144, 220 I terpene, 371, 2930 SUBJECT INDEX 3657

4,2708, terpineol, 161 thienotriazine,2766 tert-butyl hydroperoxide, 1950,2977 thiirane, 1723,2139,2140 ,1422, tert-butyl hypochlorite, 273, 1193,2571 thio-Arbuzov reaction, 1929 ,,2299, tetrabutylarnrnonium fluoride, 1452 thio-Staudinger reaction, 2643 ·,2805, tetrabutylammonium iodide, 2222 thio-Wittig reaction, 3031 tetrachlorohydroquinone, 551 thio-Wittig rearrangement, 3043 tetraethylbenzene, 1530, 1532 thioacetal, 685, 872, 3020 tetrahydrocannabinol, 850, 1363 thioacridone, 1731 l,2285, tetrahydrocarbazole, 406, 471, 472, 1073, thioamide, 1001, 1330, 1332, 1722,3021 1552, 1553 thioanisole, 537 tetrahydrofuran, 158,351,629,683,684,715, thiobenzamide, 2055 1485,1585,1609,1610,1728,1841,2826, thiocarbamate, 2392 2828 thiocarbonyldiimidazole, 239, 746, 748 tetrahydroisoquinoline, 441, 442, 443, 447, thiocarbonylimidazolide, 239 516, 1009, 1183, 1185, 1453,2210,2211, thiocyanate, 1474,2392,2393,2394,2488, 2257,3174 2490,2831,3065,3164 ~229, tetrahydroisoquinolinedione, 1183 thiocyanic acid, 3065 tetrahydropyran, 684,1165, 1693,2174, thiodiglycol, 1426, 1748 2712,2966 thiodiglycolate, 1426 tetrahydropyranone, 2173 thioester, 307, 308, 309, 1144, 1234, 1235, tetrahydropyridazine, 2218 1621,1622,1722,1754,2285 tetrahydropyridone, 515, 516, 517 thioether, 289, 307, 536, 683, 727, 762,1002, tetrahydroquinoline, 1164, 1178, 1420 1070,1127,1198,1754,1755,1935,1955, tetrahydroquinoxaline, 1264, 1266 1957,2177,2286,2363,2544,2545,2663, tetrahydrothiophene, 537 3043,3050,3165 tetralin, 339, 1345, 1530, 1564,2454,2455 thioflavone, 1722 tetralol, 2330 thioglycoside, 2498, 2499 tetralone, 550, 551, 563, 590, 1127, 1564,2315 thiohydroquinone, 1745 tetramethyllead, 2111 thiohydroxamic acid ester, 232, 233 tetranitromethane, 2759 thioimidate, 288, 2238, 2499 tetraphenylethylene, 643 thioisoflavone, 1722 tetrazine, 606, 607, 608, 609, 2905 thioisomunchnone, 919 tetrazole, 780, 2831, 2904, 2905 thioketal, 872 the 'inverse'-electron-demand Diels-Alder thioketone, 252, 678, 1722, 1723, 1857, 2067 reaction (lED), 506 thiolactone, 307, 1722 theophylline, 1410 thiolcarbonate, 2533 thermofor process, 1502 thiolysis, 1222 thermosetting resin, 160 thiomethoxymethylation, 34 thia-Brook rearrangement, 530 thionamide, 3018, 3022 thia-Fries rearrangement, 1144 thionation, 1722, 1723, 1724 thia-Payne rearrangement, 2139, 2140 thioncarbonate, 2533 thia-Wittig reaction, 3032, 3035 thionic acid, 1260, 1261 thiadiazoline, 249 thionyl chloride, 165,367,422,438, 846, 847, 4,2755 thiamin, 331, 332 1371,2423,2775,2902 thiation, 1722 thiooxazole[3,2-a]pyridinium, 511, 512 (TPD), thiazole, 1330, 1512, 1614,2198,2529 thiophene carboxylic acid, 1462 thiazolidine, 1979 thiophene, 92, 267, 410, 411, 648, 1376, 1426, thiazolidinethione, 1021, 1023,2957 1427,1516,1722,2037,2257,2421, 33 thiazolium, 14,331,332, 1935,2663,2664 2766,2872 Thiele rearrangement, 2762 thiophenol,686, 1159, 1395, 1396, 1743,2237, thienamycine, 2636 2533,2534,3130,3163,3164 thienopyrimidine, 2766 thiophsogene, 1165 3658 SUBJECT INDEX thiopseudourea, 1754 trifiuoroacetate, 1041, 1131,2193,2286,2561, thiopyranimine, 2348 2644, 3073, 3105 thiosulfate, 11,400,404,422, 1705,2265, trifiuoroacetic anhydride, 34, 165,353,355, 2720,2831 833,1894,2251,2252,2253,2256,2410, thiourea, 379, 954, 1330, 1722,2363,2734, 2982 2790,3065 trifiuoroethanol, 532, 801, 1027, 1028,2832 three center two-electron system, 69 trifluoroperoxyacetic acid, 150 thujene, 643 triformylphloroglucinol, 944 tin-Peterson reaction, 2177 trigonellin, 3174 tin-Pummerer rearrangement, 2285, 2286 trilobacin, 1609 Tishchenko reduction, 2782 trilobin, 1609 titanium tetraisopropoxide, 1706, 1707 trimethyl orthoformate, 950, 2720 titanocene, 571, 572, 2753, 2754 trimethylorthoacetate, 1562 torsional rotation, 713 trimethylsilyl cyanide, 723, 2007, 2778, 2779 tosyl azide, 2102, 2322 trimethylsilyl cyanohydrin, 723, 2778, 2853 tosylhydrazine, 196, 590 trimethylsilyl trifiuoromethanesulfonate, 1410, TPAPINMO oxidation, 2118 2444 trans-cinnamic acid, 1513 trimethylsilylacetylene, 2628, 2629 transacylation, 997 trimethylsulfoxonium iodide, 2141 transamination, 1388, 2157 trinitrobenzene, 2185 transmetalation, 1065, 1116, 1117, 1430, 1754, trioxane, 2399 1755,2029,2679,2736 trioxymethylene, 430 triacetoxyperiodinane, 871 triphenylmethane, 629, 673, 1232, 1345, 1379, trialkyl phosphite, 1929, 1930,2168 1471,2329,2676 trialkylaluminum, 3134, 3135, 3136, 3144 triphenylmethyl radical, 1238, 1239, 1242, trialkylborane, 541, 1238 2601 trialkylsilyl halide, 1107 tripheny lphosphine oxide, 523, 1956 triazene, 1669,2908,2910 triphenylphosphine, 95, 96, 97, 98, 252, 523, triazine, 609, 631,2241,2242 587,621,1955,1956,1958,2309,2140, triazole, 905,971,972, 973, 1256, 1883,2157, 2636,2642,2643,2957,3031,3032,3036 2158,2905 triphenylphosphoranylideneketene, 3031 triazolium, 1935, 1937,2663,2665 triplet quencher, 1144 tributyltin hydride, 237, 241, 531, 939, 940, triplet sensitizer, 1144 1164, 1165,2540 triplet, 823,910,1144,1464,1535,2062,2067, trichloroacetaldehyde, 2467 2068,2126,2127,2201,2610,3075 trichloroacetamide, 2100, 2101 triptycenequinone, 2764 trichloroacetimidate, 2100, 2498, 2499 tripyrrin, 2430 trichloroacetonitrile, 2100, 2102, 2237, triquinacene, 2969 2498 tris(triphenylphosphine) chlororhodium, 3011 trichloromethide, 734, 736 tris(triphenylphosphine)rhodium(l) chloride. tricyclohexylphsophine, 2308 3011 tridecane, 1232 trisulfide, 267, 1747 triethyl phosphite, 251, 585,103,1931,1954, trisulfurdichloride, 1747 2169,2170 trisyl azide, 2322 triethylaluminum, 2007, 2782, 3134, 3135, tropenone, 2799 3136,3144,3145 tropinone, 2414, 2416 triethylborane, 1165, 1239,2541,2542 tropolone, 2329 triethyloxonium hexachloroantimonate, 1877 tropone, 815, 3179 triethyloxonium hexafiuorophosphate, 1877, tropylium ion, 562 1878 Trost's ligand, 2799 triethyloxonium tetrafiuoroborate, 1877 Truce-Smiles rearrangement, 2609, 2803, 2804 triethylphosphite, 746, 2169, 3179 tryptamine, 406 SUBJECT INDEX 3659

86,2561, Tschemiac-Einhorn reagent, 2807 vinyloxytrimethylsilane, 1821 tungsten, 68, 234, 798,1066,1466,2720,2884 vitalism, 3064 l,355, Twitchell catalyst, 2817 vitamin A, 173 ,2410, Twitchell reagent, 2817, 2818, 2819 Vitamin Bl, 331 Tyrer sulfonator, 2822 vitamin B12 ',2832 vitexin, 1001, 1002 U-4C-3CR, 2830 von Braun amide degradation, 2900 U-5C-3CR, 2830 von Braun reagent, 2896 Ugi 4-center 3-component reaction, 2830 VPC, 564 Ugi five-center three-component reaction, 2830 Ugi four-center three-component reaction, 2830 Wacker catalyst, 2920 ultrasound,391,425,490,491, 743,887,1234, Wagner-Jauregg adduct, 2926 1571,1778,2152,2221,2316,2406,2630, Walden inversion, 1526, 1956,2228,2901, 18,2779 2737,2848,2874,3073 2937,2938 :,2853 undecylenic acid, 2373 Weerman test, 2946 ite, 1410, UPS strategy, 2965 Weidenhagen modification, 2294 urea-hydrogen peroxide complex, 830 Weidenhagen synthesis, 2293,2951 urea, 105, 142,351,379,382,382, 1088, 1550, Weinreb aldehyde synthesis, 2956 1722,1811,1868,2773,2789,3064,3065 Weinreb amide reduction, 2963 uredo acid, 558 Weinreb amide, 2956, 2957, 2963, 2964, 3031 urethane, 1001, 1449, 1772,2336,2712,2946 Westphalen's diol diacetate, 2988 uridine, 907, 950, 951, 2644 Westphalen's diol, 2988, 2989, 2990 45,1379, urine test, 3158 Wichterle reagent, 3003, 3004 urotropine, 865 Wilkinson's catalyst, 2346, 3011, 3012, 1242, 3013,3014 valerie acid, 364, 1646, 1829 Wittig reagent, 3031, 3032 valerie anhydride, 2190 Wittig-Horner reaction, 3031 )2,523, van Slyke apparatus, 2860 Wittig-Still rearrangement, 3049 2140, vanillin, 443 Woodward-Hofman's rule, 886 2,3036 veratraldehyde, 547, 2258 Wright-West rearrangement, 529 J3l vesicant agent, 1747 Wurtz-Fittig silylation, 3100 Vilsmeier complex, 2872 Wynberg's protocol, 2975 Vilsmeier reagent, 689, 690, 2873, 2875 xanthane, 2839 )62,2067, Vilsmeier-Haack reagent, 2872 xanthate ester, 642, 644 5 vinamidinium hexafluorophosphate salt, 149 xanthene, 2931 vindoline, 1165 xanthenocalix[6]arene, 3186 vinyl bromide, 91, 1867,2029,3004 xanthine, 2789 vinyl thioether, 1002 xanthone, 1245,2983,2984,3179 m,3011 vinylacetylene, 1710 xylene, 13, 16,516,551,632,799,892,895, iloride, vinylaziridine, 308, 2882 1317,1319,2284,2343,3115,3146 vinylcyclopropane, 806, 2880, 2881, 2882, xylose, 761, 1089,2983 2883,2884 vinyldihydrofuran,2164 Yamaguchi reagent, 3109, 3110 vinylketene, 797, 934 yellow cross, 1747 vinylogous Mannich reaction, 1820 ynamine,820 vinylogous Pictet-Spengler cyclization, 2211 ynone,2956 vinylogous pinacol rearrangement, 2228 yohimbine, 35, 2195 vinylogous Pummerer reaction, 2285 yohimbinone, 2195 vinylogous Reformatsky reaction, 2315 yperite, 1747 vinylogous tin-Pummerer rearrangement, 2286 ~03, 2804 vinylogous Wolff rearrangement, 3076 Zaitsev product, 2480 vinyloxirane, 308, 1777 zearaIenone, 1860 3660 SUBJECT INDEX zearolone, 2680 a-hydroxy ketone, 13, 18, 872, 1564, 1676, Zeise's dimmer, 1048 1857,1872,2442,2951 Zelinsky-Stadnikoff reagent, 3119 a-hydroxyamine, 1403 zeolite, 151, 1127, 1132, 1144, 1622, 1872, a-hydroxyketone, 406, 1172, 2442, 2952 1893, 1894,2063,2067,2201,2202,2284, a-isocyano Weinreb amide, 2956 2446,3068 a-keto oxime, 1110 Ziegler alcohol, 3134, 3144 o-ketoaldehyde, 2969 Ziegler alumina, 3135 e-ketoamide, 1962, 1963, 2221 Ziegler catalyst, 3134 o-ketoamine, 1403 Ziegler-Natta catalyst, 3144, 3145, 3147, a-ketoglutaric acid, 1390 3150 e-ketolactam, 516 Zimmermann chromogen, 3158 o-ketonitrile, 1213 zinc amalgam, 1260 a-methylbutyric acid, 1831 zinc chloride, 66, 362, 364,410,420,422,429, a-naphthoquinone, 2762 430,431,924,1202,2035,2039 a-naphthylamine, 553 Zincke aldehyde, 3172 o-nitronaphthalene, 2244, 2246 Zincke salt, 3174 o-picoline, 894, 895 Zinke-Cornforth procedure, 3184, 3185 a-pinene, 538,540, 2102 zirconacycle, 570, 571 a-piperidyl-4-quinolinemethanol, 25 zirconaoxirane, 2222 a-pyridylcarbinol, 1314 zirconia, 2097, 2495 a-pyrone ring, 1679 zirconium-Negishi reaction, 2029 a-surfhydryl ketone, 107 zirconium, chlorobis(1]5-2,4-cyclopentadien­ e-tetralone, 551, 2315 I-yl)hydro, 2540 o-thiol acid, 1260 zirconocene hydrochloride, 2540 o-thiolation. 107 zwitterion, 307, 1262, 1314,2702 a,a,a-triftuoroacetophenone, 1985 a,a'-dibromopimelate, 1115 a-amino aldehyde, 29, 30, 2965 a,~-enone, 1155, 1583,2975,2976 a-amino ketone, 272, 332,833, 1302, 1303, a,~-epoxyketone, 1005, 1583 1634,1635,2017,2088,2704,2889 a,~-unsaturated I)-lactone, 1217 a-amino phosphonate, 1588, 1589 o-aminobutyrolactone, 2831 ~-aminopropenal, 311 a-aminoisobutyric acid, 1388 ~-cyclodextrin, 1144 a-aminoketone, 677, 2888, 2890 ~-diester, 1687 a-aminophenylacetic acid, 1390 ~-dihydrothebainol, 2267 a-azido acid, 734, 735 ~-diketone, 168,170,303,688,819,858,1871, a-bromoester, 424, 2314, 2315 2233,2234,2695,2983,2984,3130,3147, o-bromoethylamine, I ]80 3148,3150 o-bromoketone, 1113, 1695, 1845,2169,3004 ~-gentiobiose, 1086 a-bromolactone, 2315 ~-hydride elimination, 1351 o-chloroacetophenone. 1750, 2722 ~-hydroxysulfone, 1576 rz-chlorocyclohexanone, 407 ~-keto ester, 5, 6, 7, 376, 379, 424, 425, 426, a-chloromethyl ketone, 2058, 2059, 2963 567,569,625,677,858,859,881,939, o-diazoindanone, 3074 1036,1322,1326,1687,1722,1871,2233, a-diazoketone, 3073, 3074, 3075, 3076 2234,2315,2491,2492 a-elimination, 1151, 3095 ~-ketoamide, 1621 e-haloamine, 1180 ~-ketoester, 9,303,611, 612, 692, 693,881, o-halohydrin, 2228, 2229 1036,1321,1326,1621,1635,1638,1801, a-haloketone, 111,406,855, 1036, 1037, 1812,1901,1902,1922,2814,2963 1330, 1331, 2980 ~-Iactam, 426, 517, 519, 521, 522, 523,819, o-halosulfonc, 2298 822,1165,1222,1234,1235,1723,1979, a-hydroxy epoxide, 2228, 2229 2636,2637,2638,2639,2831 SUBJECT INDEX 3661

4,1676, ,B-naphthisatin, 1838 v-pyrone, 147, 149 ,B-naphthol, 374, 375,553,554,555,947, 1269 8-lactone, 454, 1217, 1426 2952 ,B-picoline,3174 8-phenylvaleramide, 3022 ,B-truxinicacid, 820 8-valerolactone,446

y-alumina, 3135 s-caprolactam, 288 y-bromocrotonate, 2315 s-caprolactone, 1014 y-bromocrotonic acid, 1977 y-butyrolactone, 788, 1812,2317 IT-complex, 1l31, 1517,3012 y-diketone, 6 y-hydroxyenone, 1675, 1677 a-complex, ]]31, 1132 y-Iactone, 1Ol3, 1615,2315,2686,2687, 2826,2827 w-dimethylaminoacetophenone, 678

~5

~,858, 1871, 130,3147,

425,426, I, 939, 871, 2233,

693,881, 638,1801, ~963 523,819, '23,1979,