31:
537:
Cameron, T Stanley; Clyburne, Jason AC; Dubey, Pramod K.; Grossert, J Stuart; Ramaiah, K.; Ramanatham, J.; Sereda, Sergei V. (2003). "Compounds of chromium(VI): The
PyridineChromic Anhydride Complex, Benzimidazolinium Dichromate, and Three 2-Alkyl-1H-benzimidazolinium Dichromates".
1611:
405:
The application of this reagent to oxidations was discovered by G. I. Poos, G. E. Arth, R. E. Beyler and L.H. Sarett in 1953. It was popularized by J. C. Collins several years later.
3826:
366:
Like other oxidations by Cr(VI), the stoichiometry of the oxidations is complex because the metal undergoes 3e reduction and the substrate is oxidized by 2 electrons:
2942:
2887:
3655:
2997:
565:
Sisler, Harry H.; Bush, Jack D.; Accountius, Oliver E. (1948). "Addition
Compounds of Chromic Anhydride with Some Heterocyclic Nitrogen Bases".
3147:
1781:
3876:
355:
Collins reagent is especially useful for oxidations of acid sensitive compounds. Primary and secondary alcohols are oxidized respectively to
3650:
1476:
195:
344:, the complex is 5-coordinate with mutually trans pyridine ligands. The Cr-O and Cr-N distances are respectively 163 and 215 picometers.
2752:
673:
419:
3322:
2522:
1266:
3487:
3417:
3397:
2892:
2059:
1521:
1940:
1496:
709:
3242:
3720:
3670:
2074:
600:
Ronald
Ratcliffe and Ronald Rodehorst (1970). "Improved Procedure for Oxidations with the Chromium Trioxide-Pyridine Complex".
101:
3177:
3816:
3625:
3282:
3262:
3222:
2029:
972:
628:
J. C. Collins, W. W. Hess and F. J. Frank (1968). "Dipyridine-chromium(VI) oxide oxidation of alcohols in dichloromethane".
3811:
3741:
3640:
3297:
3152:
2782:
2627:
2237:
1864:
1641:
3891:
3675:
2987:
2477:
2152:
2697:
3886:
3600:
3462:
3252:
3217:
3776:
3715:
3247:
3162:
3132:
3112:
2977:
2972:
2347:
2272:
1915:
1869:
1736:
997:
160:
3881:
3841:
3791:
3467:
3267:
3017:
2947:
1436:
1007:
3082:
1975:
1696:
510:
J. C. Collins, W.W. Hess (1972). "Aldehydes from
Primary Alcohols by Oxidation with Chromium Trioxide: Heptanal".
281:
3975:
3635:
3477:
3347:
3342:
3157:
2632:
2542:
2132:
2064:
1955:
1531:
1286:
1211:
666:
3392:
3921:
3806:
3705:
3645:
3292:
3087:
3047:
3022:
2932:
2392:
1426:
1356:
992:
922:
491:
340:
The complex is produced by treating chromium trioxide with pyridine. The complex is diamagnetic. According to
2512:
3911:
3497:
3387:
3007:
2732:
2517:
2462:
2307:
2267:
2099:
1854:
1571:
1421:
3871:
3432:
2877:
3906:
3821:
3796:
3771:
3756:
3680:
3595:
3492:
3452:
3317:
3272:
3037:
2582:
2567:
2432:
2222:
1890:
1646:
1326:
1301:
1271:
862:
3856:
3801:
3746:
3457:
3377:
3277:
2992:
2957:
2802:
2692:
2407:
2402:
2227:
2187:
2084:
1895:
1859:
1711:
1701:
1556:
1416:
1276:
1226:
1221:
1196:
1156:
1102:
867:
857:
832:
3831:
3532:
3337:
2772:
2657:
2337:
2312:
2252:
2109:
1844:
1551:
1331:
1296:
1201:
892:
827:
659:
3122:
1386:
3970:
3931:
3836:
3690:
3570:
3542:
3512:
3427:
3357:
3312:
3287:
3207:
3107:
3067:
2762:
2382:
2372:
2297:
1821:
1681:
1676:
1656:
1341:
1138:
1117:
1077:
1002:
430:
822:
179:
InChI=1/2C5H5N.Cr.3O/c2*1-2-4-6-5-3-1;;;;/h2*1-5H;;;;/r2C5H5N.CrO3/c2*1-2-4-6-5-3-1;2-1(3)4/h2*1-5H;
3896:
3786:
3766:
3630:
3472:
3382:
3352:
3332:
3227:
3182:
3012:
2922:
2852:
2737:
2727:
2557:
2114:
2054:
2019:
1826:
1806:
1766:
1541:
1411:
1376:
1336:
1087:
927:
917:
847:
3362:
3866:
3725:
3575:
3517:
3442:
3422:
3142:
3092:
2952:
2917:
2857:
2787:
2342:
2089:
2069:
1801:
1721:
1616:
1576:
1546:
1481:
1366:
1351:
1261:
1251:
912:
837:
792:
1127:
3605:
3327:
3077:
3057:
3032:
2982:
2897:
2872:
2827:
2797:
2777:
2747:
2712:
2667:
2642:
2617:
2502:
2427:
2207:
1900:
1836:
1636:
1361:
1281:
967:
942:
719:
714:
309:
3941:
3527:
3482:
3197:
3167:
3137:
3072:
3052:
2967:
2962:
2927:
2882:
2867:
2862:
2842:
2832:
2767:
2757:
2687:
2637:
2157:
1960:
1536:
1491:
1321:
1311:
1057:
982:
777:
739:
438:
341:
43:
987:
3710:
3660:
3610:
3590:
3580:
3437:
3412:
3127:
3117:
3002:
2817:
2812:
2742:
2527:
2327:
2287:
2217:
2182:
2137:
2104:
1970:
1945:
1925:
1746:
1706:
1666:
1631:
1561:
1316:
1186:
1161:
699:
121:
77:
8:
3916:
3901:
3547:
3522:
3507:
3502:
3232:
3187:
3172:
3062:
3042:
2937:
2822:
2807:
2652:
2597:
2587:
2552:
2317:
2192:
2167:
2079:
1935:
1920:
1905:
1726:
1671:
1441:
1291:
1236:
1107:
1022:
882:
807:
67:
3926:
2577:
1761:
952:
3665:
3615:
3585:
3447:
3237:
3027:
2912:
2847:
2837:
2602:
2532:
2497:
2492:
2472:
2467:
2412:
2322:
2172:
2034:
2024:
1930:
1716:
1661:
1591:
1511:
1406:
1306:
1241:
1166:
1012:
877:
812:
797:
399:
321:
642:
449:
The solid is flammable. Generally speaking chromium (VI) compounds are carcinogenic.
3402:
2722:
2607:
2572:
2537:
2482:
2437:
2352:
2332:
2282:
2277:
2247:
2232:
2142:
2049:
1985:
1950:
1776:
1651:
1526:
1451:
1431:
1346:
1181:
1176:
1122:
1032:
937:
897:
852:
734:
729:
694:
630:
582:
487:
313:
297:
17:
2397:
3936:
3781:
3751:
3695:
3620:
3552:
3307:
3257:
3102:
2907:
2682:
2677:
2622:
2612:
2387:
2197:
2177:
2147:
2044:
1980:
1965:
1796:
1751:
1741:
1731:
1626:
1606:
1601:
1586:
1581:
1461:
1456:
1396:
1381:
1371:
1216:
1206:
1072:
1062:
962:
957:
932:
872:
724:
683:
638:
610:
574:
547:
519:
479:
414:
218:
1052:
146:
3846:
3537:
3372:
3367:
2662:
2647:
2592:
2547:
2507:
2457:
2422:
2417:
2362:
2357:
2292:
2242:
2162:
1990:
1874:
1849:
1811:
1786:
1771:
1756:
1691:
1566:
1516:
1506:
1486:
1446:
1256:
1246:
1231:
1027:
947:
817:
787:
772:
767:
305:
3851:
3761:
3700:
2792:
2702:
2672:
2447:
2302:
2039:
1816:
1686:
1501:
1471:
1171:
1067:
842:
704:
275:
651:
483:
3964:
3861:
3562:
3407:
3302:
3097:
2487:
2452:
2442:
2377:
2367:
2257:
2094:
1910:
1621:
1596:
1466:
1112:
1097:
1082:
977:
907:
887:
802:
602:
523:
426:
16:
This article is about the oxidizing reagent. For the oxidation reaction, see
2902:
2262:
2014:
1791:
1391:
1191:
1042:
1037:
902:
757:
586:
1401:
1047:
1017:
782:
627:
329:
614:
578:
3685:
3212:
2562:
245:
112:
599:
356:
347:
In terms of history, the complex was first produced by Sisler et al.
317:
551:
274:
Except where otherwise noted, data are given for materials in their
1092:
762:
301:
100:
30:
752:
360:
325:
263:
133:
434:
402:
is the typical solvent, with the solubility of 12.5 g/100 ml.
90:
536:
441:(PDC) oxidations have largely supplanted Collins oxidation.
474:
Fillmore
Freeman (2001). "Dipyridine Chromium(VI) Oxide".
509:
169:
InChI=1S/2C5H5N.Cr.3O/c2*1-2-4-6-5-3-1;;;;/h2*1-5H;;;;
476:
e-EROS Encyclopedia of
Reagents for Organic Synthesis
425:
Collins reagent can be used as an alternative to the
3827:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
564:
444:
398:The reagent is typically used in a sixfold excess.
2888:Divinylcyclopropane-cycloheptadiene rearrangement
3962:
473:
145:
681:
76:
3148:Thermal rearrangement of aromatic hydrocarbons
1782:Thermal rearrangement of aromatic hydrocarbons
3877:Lectka enantioselective beta-lactam synthesis
1137:
667:
3656:Inverse electron-demand Diels–Alder reaction
1477:Heterogeneous metal catalyzed cross-coupling
2998:Lobry de Bruyn–Van Ekenstein transformation
433:(PCC) when oxidizing secondary alcohols to
420:Oxidation with chromium(VI)-amine complexes
674:
660:
335:
120:
3488:Petrenko-Kritschenko piperidone synthesis
2943:Fritsch–Buttenberg–Wiechell rearrangement
3651:Intramolecular Diels–Alder cycloaddition
567:Journal of the American Chemical Society
3963:
3671:Metal-centered cycloaddition reactions
3323:Debus–Radziszewski imidazole synthesis
1267:Bodroux–Chichibabin aldehyde synthesis
469:
467:
465:
463:
461:
3817:Diazoalkane 1,3-dipolar cycloaddition
3721:Vinylcyclopropane (5+2) cycloaddition
3626:Diazoalkane 1,3-dipolar cycloaddition
3398:Hurd–Mori 1,2,3-thiadiazole synthesis
2893:Dowd–Beckwith ring-expansion reaction
2060:Hurd–Mori 1,2,3-thiadiazole synthesis
1136:
973:LFER solvent coefficients (data page)
655:
505:
503:
172:Key: NPRDHMWYZHSAHR-UHFFFAOYSA-N
2628:Sharpless asymmetric dihydroxylation
1865:Methoxymethylenetriphenylphosphorane
2753:Allen–Millar–Trippett rearrangement
458:
182:Key: NPRDHMWYZHSAHR-RGHLCDNPAM
136:
13:
3892:Nitrone-olefin (3+2) cycloaddition
3887:Niementowski quinazoline synthesis
3676:Nitrone-olefin (3+2) cycloaddition
3601:Azide-alkyne Huisgen cycloaddition
3463:Niementowski quinazoline synthesis
3218:Azide-alkyne Huisgen cycloaddition
2523:Meerwein–Ponndorf–Verley reduction
2075:Leimgruber–Batcho indole synthesis
500:
14:
3987:
3716:Trimethylenemethane cycloaddition
3418:Johnson–Corey–Chaykovsky reaction
3283:Cadogan–Sundberg indole synthesis
3263:Bohlmann–Rahtz pyridine synthesis
3223:Baeyer–Emmerling indole synthesis
2030:Cadogan–Sundberg indole synthesis
1522:Johnson–Corey–Chaykovsky reaction
408:
3812:Cook–Heilbron thiazole synthesis
3641:Hexadehydro Diels–Alder reaction
3468:Niementowski quinoline synthesis
3298:Cook–Heilbron thiazole synthesis
3243:Bischler–Möhlau indole synthesis
3153:Tiffeneau–Demjanov rearrangement
2783:Baker–Venkataraman rearrangement
1941:Horner–Wadsworth–Emmons reaction
1612:Mizoroki-Heck vs. Reductive Heck
1497:Horner–Wadsworth–Emmons reaction
1008:Neighbouring group participation
445:Safety and environmental aspects
29:
3348:Fiesselmann thiophene synthesis
3178:Westphalen–Lettré rearrangement
3158:Vinylcyclopropane rearrangement
2988:Kornblum–DeLaMare rearrangement
2633:Epoxidation of allylic alcohols
2543:Noyori asymmetric hydrogenation
2478:Kornblum–DeLaMare rearrangement
2153:Gallagher–Hollander degradation
278:(at 25 °C , 100 kPa).
47:Pyridine - trioxochromium (2:1)
3807:Chichibabin pyridine synthesis
3293:Chichibabin pyridine synthesis
3253:Blum–Ittah aziridine synthesis
3088:Ring expansion and contraction
1357:Cross dehydrogenative coupling
621:
593:
558:
530:
1:
3777:Bischler–Napieralski reaction
3735:Heterocycle forming reactions
3388:Hemetsberger indole synthesis
3248:Bischler–Napieralski reaction
3163:Wagner–Meerwein rearrangement
3133:Sommelet–Hauser rearrangement
3113:Seyferth–Gilbert homologation
2978:Ireland–Claisen rearrangement
2973:Hofmann–Martius rearrangement
2733:2,3-sigmatropic rearrangement
2348:Corey–Winter olefin synthesis
2273:Barton–McCombie deoxygenation
1916:Corey–Winter olefin synthesis
1870:Seyferth–Gilbert homologation
1737:Seyferth–Gilbert homologation
643:10.1016/S0040-4039(00)89494-0
540:Canadian Journal of Chemistry
452:
55:Dipyridine chromium(VI) oxide
3882:Lehmstedt–Tanasescu reaction
3842:Gabriel–Colman rearrangement
3797:Bucherer carbazole synthesis
3792:Borsche–Drechsel cyclization
3772:Bernthsen acridine synthesis
3757:Bamberger triazine synthesis
3742:Algar–Flynn–Oyamada reaction
3453:Nazarov cyclization reaction
3318:De Kimpe aziridine synthesis
3273:Bucherer carbazole synthesis
3268:Borsche–Drechsel cyclization
3038:Nazarov cyclization reaction
3018:Meyer–Schuster rearrangement
2948:Gabriel–Colman rearrangement
2698:Wolffenstein–Böters reaction
2583:Reduction of nitro compounds
2433:Grundmann aldehyde synthesis
2238:Algar–Flynn–Oyamada reaction
1647:Olefin conversion technology
1642:Nozaki–Hiyama–Kishi reaction
1437:Gabriel–Colman rearrangement
1327:Claisen-Schmidt condensation
1272:Bouveault aldehyde synthesis
350:
7:
3857:Hantzsch pyridine synthesis
3636:Enone–alkene cycloadditions
3458:Nenitzescu indole synthesis
3378:Hantzsch pyridine synthesis
3343:Ferrario–Ackermann reaction
2993:Kowalski ester homologation
2958:Halogen dance rearrangement
2803:Benzilic acid rearrangement
2228:Akabori amino-acid reaction
2188:Von Braun amide degradation
2133:Barbier–Wieland degradation
2085:Nenitzescu indole synthesis
2065:Kharasch–Sosnovsky reaction
1956:Julia–Kocienski olefination
1860:Kowalski ester homologation
1557:Kowalski ester homologation
1532:Julia–Kocienski olefination
1287:Cadiot–Chodkiewicz coupling
1212:Aza-Baylis–Hillman reaction
1157:Acetoacetic ester synthesis
868:Dynamic binding (chemistry)
858:Conrotatory and disrotatory
833:Charge remote fragmentation
10:
3992:
3922:Robinson–Gabriel synthesis
3872:Kröhnke pyridine synthesis
3706:Retro-Diels–Alder reaction
3646:Imine Diels–Alder reaction
3433:Kröhnke pyridine synthesis
3048:Newman–Kwart rearrangement
3023:Mislow–Evans rearrangement
2933:Fischer–Hepp rearrangement
2878:Di-Ď€-methane rearrangement
2658:Stephen aldehyde synthesis
2393:Eschweiler–Clarke reaction
2110:Williamson ether synthesis
1427:Fujiwara–Moritani reaction
1332:Combes quinoline synthesis
1297:Carbonyl olefin metathesis
998:More O'Ferrall–Jencks plot
923:Grunwald–Winstein equation
893:Electron-withdrawing group
828:Catalytic resonance theory
312:, a red solid, is used to
203:c1ccncc1.c1ccncc1.O=(=O)=O
15:
3932:Urech hydantoin synthesis
3912:Pomeranz–Fritsch reaction
3837:Fischer oxazole synthesis
3734:
3571:1,3-Dipolar cycloaddition
3561:
3543:Urech hydantoin synthesis
3513:Reissert indole synthesis
3498:Pomeranz–Fritsch reaction
3428:Knorr quinoline synthesis
3358:Fischer oxazole synthesis
3288:Camps quinoline synthesis
3208:1,3-Dipolar cycloaddition
3196:
3108:Semipinacol rearrangement
3083:Ramberg–Bäcklund reaction
3068:Piancatelli rearrangement
3008:McFadyen–Stevens reaction
2763:Alpha-ketol rearrangement
2711:
2518:McFadyen–Stevens reaction
2463:Kiliani–Fischer synthesis
2383:Elbs persulfate oxidation
2308:Bouveault–Blanc reduction
2268:Baeyer–Villiger oxidation
2206:
2123:
2100:Schotten–Baumann reaction
2003:
1976:Ramberg–Bäcklund reaction
1883:
1855:Kiliani–Fischer synthesis
1835:
1697:Ramberg–Bäcklund reaction
1682:Pinacol coupling reaction
1677:Piancatelli rearrangement
1572:Liebeskind–Srogl coupling
1422:Fujimoto–Belleau reaction
1145:
1139:List of organic reactions
1003:Negative hyperconjugation
748:
690:
484:10.1002/047084289X.rd452m
431:pyridinium chlorochromate
272:
211:
191:
156:
60:
52:
42:
37:
28:
3907:Pictet–Spengler reaction
3822:Einhorn–Brunner reaction
3787:Boger pyridine synthesis
3681:Oxo-Diels–Alder reaction
3596:Aza-Diels–Alder reaction
3493:Pictet–Spengler reaction
3393:Hofmann–Löffler reaction
3383:Hegedus indole synthesis
3353:Fischer indole synthesis
3228:Bartoli indole synthesis
3183:Willgerodt rearrangement
3013:McLafferty rearrangement
2923:Ferrier carbocyclization
2738:2,3-Wittig rearrangement
2728:1,2-Wittig rearrangement
2568:Parikh–Doering oxidation
2558:Oxygen rebound mechanism
2223:Adkins–Peterson reaction
2115:Yamaguchi esterification
2055:Hegedus indole synthesis
2020:Bartoli indole synthesis
1891:Bamford–Stevens reaction
1807:Weinreb ketone synthesis
1767:Stork enamine alkylation
1542:Knoevenagel condensation
1412:Ferrier carbocyclization
1302:Castro–Stephens coupling
928:Hammett acidity function
918:Free-energy relationship
863:Curtin–Hammett principle
848:Conformational isomerism
524:10.15227/orgsyn.052.0005
314:oxidize primary alcohols
3867:Knorr pyrrole synthesis
3802:Bucherer–Bergs reaction
3747:Allan–Robinson reaction
3726:Wagner-Jauregg reaction
3518:Ring-closing metathesis
3443:Larock indole synthesis
3423:Knorr pyrrole synthesis
3278:Bucherer–Bergs reaction
3143:Stieglitz rearrangement
3123:Skattebøl rearrangement
3093:Ring-closing metathesis
2953:Group transfer reaction
2918:Favorskii rearrangement
2858:Cornforth rearrangement
2788:Bamberger rearrangement
2693:Wolff–Kishner reduction
2513:Markó–Lam deoxygenation
2408:Fleming–Tamao oxidation
2403:Fischer–Tropsch process
2090:Oxymercuration reaction
2070:Knorr pyrrole synthesis
1896:Barton–Kellogg reaction
1802:Wagner-Jauregg reaction
1722:Ring-closing metathesis
1712:Reimer–Tiemann reaction
1702:Rauhut–Currier reaction
1617:Nef isocyanide reaction
1577:Malonic ester synthesis
1547:Knorr pyrrole synthesis
1482:High dilution principle
1417:Friedel–Crafts reaction
1352:Cross-coupling reaction
1277:Bucherer–Bergs reaction
1262:Blanc chloromethylation
1252:Blaise ketone synthesis
1227:Baylis–Hillman reaction
1222:Barton–Kellogg reaction
1197:Allan–Robinson reaction
1103:Woodward–Hoffmann rules
838:Charge-transfer complex
336:Synthesis and structure
3976:Chromium(VI) compounds
3832:Feist–Benary synthesis
3606:Bradsher cycloaddition
3576:4+4 Photocycloaddition
3533:Simmons–Smith reaction
3478:Paternò–Büchi reaction
3338:Feist–Benary synthesis
3328:Dieckmann condensation
3078:Pummerer rearrangement
3058:Oxy-Cope rearrangement
3033:Myers allene synthesis
2983:Jacobsen rearrangement
2898:Electrocyclic reaction
2873:Demjanov rearrangement
2828:Buchner ring expansion
2798:Beckmann rearrangement
2778:Aza-Cope rearrangement
2773:Arndt–Eistert reaction
2748:Alkyne zipper reaction
2668:Transfer hydrogenation
2643:Sharpless oxyamination
2618:Selenoxide elimination
2503:Lombardo methylenation
2428:Griesbaum coozonolysis
2338:Corey–Itsuno reduction
2313:Boyland–Sims oxidation
2253:Angeli–Rimini reaction
1901:Boord olefin synthesis
1845:Arndt–Eistert reaction
1837:Homologation reactions
1637:Nitro-Mannich reaction
1552:Kolbe–Schmitt reaction
1362:Cross-coupling partner
1282:Buchner ring expansion
1202:Arndt–Eistert reaction
968:Kinetic isotope effect
715:Rearrangement reaction
310:metal-pyridine complex
3691:Pauson–Khand reaction
3528:Sharpless epoxidation
3483:Pechmann condensation
3363:Friedländer synthesis
3313:Davis–Beirut reaction
3168:Wallach rearrangement
3138:Stevens rearrangement
3073:Pinacol rearrangement
3053:Overman rearrangement
2968:Hofmann rearrangement
2963:Hayashi rearrangement
2928:Ferrier rearrangement
2883:Dimroth rearrangement
2868:Curtius rearrangement
2863:Criegee rearrangement
2843:Claisen rearrangement
2833:Carroll rearrangement
2768:Amadori rearrangement
2758:Allylic rearrangement
2638:Sharpless epoxidation
2373:Dess–Martin oxidation
2298:Bohn–Schmidt reaction
2158:Hofmann rearrangement
1961:Kauffmann olefination
1884:Olefination reactions
1822:Wurtz–Fittig reaction
1657:Palladium–NHC complex
1537:Kauffmann olefination
1492:Homologation reaction
1342:Corey–House synthesis
1322:Claisen rearrangement
1118:Yukawa–Tsuno equation
1078:Swain–Lupton equation
1058:Spherical aromaticity
993:Möbius–Hückel concept
778:Aromatic ring current
740:Substitution reaction
439:pyridinium dichromate
363:in yields of 87-98%.
342:X-ray crystallography
328:. This complex is a
324:to the corresponding
316:to the corresponding
250:258.194
3897:Paal–Knorr synthesis
3767:Barton–Zard reaction
3711:Staudinger synthesis
3661:Ketene cycloaddition
3631:Diels–Alder reaction
3611:Cheletropic reaction
3591:Alkyne trimerisation
3473:Paal–Knorr synthesis
3438:Kulinkovich reaction
3413:Jacobsen epoxidation
3333:Diels–Alder reaction
3128:Smiles rearrangement
3118:Sigmatropic reaction
3003:Lossen rearrangement
2853:Corey–Fuchs reaction
2818:Boekelheide reaction
2813:Bergmann degradation
2743:Achmatowicz reaction
2528:Methionine sulfoxide
2328:Clemmensen reduction
2288:Bergmann degradation
2218:Acyloin condensation
2183:Strecker degradation
2138:Bergmann degradation
2105:Ullmann condensation
1971:Peterson olefination
1946:Hydrazone iodination
1926:Elimination reaction
1827:Zincke–Suhl reaction
1747:Sonogashira coupling
1707:Reformatsky reaction
1667:Peterson olefination
1632:Nierenstein reaction
1562:Kulinkovich reaction
1377:Diels–Alder reaction
1337:Corey–Fuchs reaction
1317:Claisen condensation
1187:Alkyne trimerisation
1162:Acyloin condensation
1128:ÎŁ-bishomoaromaticity
1088:Thorpe–Ingold effect
700:Elimination reaction
3917:Prilezhaev reaction
3902:Pellizzari reaction
3581:(4+3) cycloaddition
3548:Van Leusen reaction
3523:Robinson annulation
3508:Pschorr cyclization
3503:Prilezhaev reaction
3233:Bergman cyclization
3188:Wolff rearrangement
3173:Weerman degradation
3063:Pericyclic reaction
3043:Neber rearrangement
2938:Fries rearrangement
2823:Brook rearrangement
2808:Bergman cyclization
2653:Staudinger reaction
2598:Rosenmund reduction
2588:Reductive amination
2553:Oppenauer oxidation
2343:Corey–Kim oxidation
2318:Cannizzaro reaction
2193:Weerman degradation
2168:Isosaccharinic acid
2080:Mukaiyama hydration
1936:Hofmann elimination
1921:Dehydrohalogenation
1906:Chugaev elimination
1727:Robinson annulation
1672:Pfitzinger reaction
1442:Gattermann reaction
1387:Wulff–Dötz reaction
1367:Dakin–West reaction
1292:Carbonyl allylation
1237:Bergman cyclization
1023:Kennedy J. P. Orton
943:Hammond's postulate
913:Flippin–Lodge angle
883:Electromeric effect
808:Beta-silicon effect
793:Baker–Nathan effect
615:10.1021/jo00836a108
579:10.1021/ja01191a085
25:
3666:McCormack reaction
3616:Conia-ene reaction
3448:Madelung synthesis
3238:Biginelli reaction
3028:Mumm rearrangement
2913:Favorskii reaction
2848:Cope rearrangement
2838:Chan rearrangement
2603:Rubottom oxidation
2533:Miyaura borylation
2498:Lipid peroxidation
2493:Lindgren oxidation
2473:Kornblum oxidation
2468:Kolbe electrolysis
2413:Fukuyama reduction
2323:Carbonyl reduction
2173:Marker degradation
2035:Diazonium compound
2025:Boudouard reaction
2004:Carbon-heteroatom
1931:Grieco elimination
1717:Rieche formylation
1662:Passerini reaction
1592:Meerwein arylation
1512:Hydroxymethylation
1407:Favorskii reaction
1307:Chan rearrangement
1242:Biginelli reaction
1167:Aldol condensation
1013:2-Norbornyl cation
988:Möbius aromaticity
983:Markovnikov's rule
878:Effective molarity
823:Bürgi–Dunitz angle
813:Bicycloaromaticity
400:Methylene chloride
322:secondary alcohols
298:chromium(VI) oxide
296:is the complex of
282:Infobox references
23:
3958:
3957:
3954:
3953:
3950:
3949:
3942:Wohl–Aue reaction
3586:6+4 Cycloaddition
3403:Iodolactonization
2723:1,2-rearrangement
2688:Wohl–Aue reaction
2608:Sabatier reaction
2573:Pinnick oxidation
2538:Mozingo reduction
2483:Leuckart reaction
2438:Haloform reaction
2353:Criegee oxidation
2333:Collins oxidation
2283:Benkeser reaction
2278:Bechamp reduction
2248:Andrussow process
2233:Alcohol oxidation
2143:Edman degradation
2050:Haloform reaction
1999:
1998:
1986:Takai olefination
1951:Julia olefination
1777:Takai olefination
1652:Olefin metathesis
1527:Julia olefination
1452:Grignard reaction
1432:Fukuyama coupling
1347:Coupling reaction
1312:Chan–Lam coupling
1182:Alkyne metathesis
1177:Alkane metathesis
1033:Phosphaethynolate
938:George S. Hammond
898:Electronic effect
853:Conjugated system
735:Stereospecificity
730:Stereoselectivity
695:Addition reaction
684:organic reactions
637:(30): 3363–3366.
631:Tetrahedron Lett.
609:(11): 4000–4001.
573:(11): 3827–3830.
512:Organic Syntheses
290:Chemical compound
288:
287:
102:Interactive image
18:Collins oxidation
3983:
3971:Oxidizing agents
3937:Wenker synthesis
3927:Stollé synthesis
3782:Bobbitt reaction
3752:Auwers synthesis
3696:Povarov reaction
3621:Cyclopropanation
3559:
3558:
3553:Wenker synthesis
3308:Darzens reaction
3258:Bobbitt reaction
3103:Schmidt reaction
2908:Enyne metathesis
2683:Whiting reaction
2678:Wharton reaction
2623:Shapiro reaction
2613:Sarett oxidation
2578:Prévost reaction
2388:Emde degradation
2198:Wohl degradation
2178:Ruff degradation
2148:Emde degradation
2045:Grignard reagent
1981:Shapiro reaction
1966:McMurry reaction
1833:
1832:
1797:Ullmann reaction
1762:Stollé synthesis
1752:Stetter reaction
1742:Shapiro reaction
1732:Sakurai reaction
1627:Negishi coupling
1607:Minisci reaction
1602:Michael reaction
1587:McMurry reaction
1582:Mannich reaction
1462:Hammick reaction
1457:Grignard reagent
1397:Enyne metathesis
1382:Doebner reaction
1372:Darzens reaction
1217:Barbier reaction
1207:Auwers synthesis
1134:
1133:
1108:Woodward's rules
1073:Superaromaticity
1063:Spiroaromaticity
963:Inductive effect
958:Hyperconjugation
933:Hammett equation
873:Edwards equation
725:Regioselectivity
676:
669:
662:
653:
652:
647:
646:
625:
619:
618:
597:
591:
590:
562:
556:
555:
534:
528:
527:
507:
498:
497:
471:
415:Sarett oxidation
219:Chemical formula
149:
138:
124:
104:
80:
33:
26:
24:Collins reagent
22:
3991:
3990:
3986:
3985:
3984:
3982:
3981:
3980:
3961:
3960:
3959:
3946:
3847:Gewald reaction
3730:
3557:
3538:Skraup reaction
3373:Graham reaction
3368:Gewald reaction
3199:
3192:
2714:
2707:
2663:Swern oxidation
2648:Stahl oxidation
2593:Riley oxidation
2548:Omega oxidation
2508:Luche reduction
2458:Jones oxidation
2423:Glycol cleavage
2418:Ganem oxidation
2363:Davis oxidation
2358:Dakin oxidation
2293:Birch reduction
2243:Amide reduction
2209:
2202:
2163:Hooker reaction
2125:
2119:
2007:
2005:
1995:
1991:Wittig reaction
1879:
1875:Wittig reaction
1850:Hooker reaction
1831:
1812:Wittig reaction
1787:Thorpe reaction
1772:Suzuki reaction
1757:Stille reaction
1692:Quelet reaction
1567:Kumada coupling
1517:Ivanov reaction
1507:Hydrovinylation
1487:Hiyama coupling
1447:Glaser coupling
1257:Blaise reaction
1247:Bingel reaction
1232:Benary reaction
1149:
1147:
1141:
1132:
1028:Passive binding
948:Homoaromaticity
798:Baldwin's rules
773:Antiaromaticity
768:Anomeric effect
744:
686:
680:
650:
626:
622:
598:
594:
563:
559:
552:10.1139/v03-042
535:
531:
508:
501:
494:
472:
459:
455:
447:
411:
393:
389:
385:
381:
377:
373:
353:
338:
306:dichloromethane
294:Collins reagent
291:
284:
279:
239:
235:
231:
227:
221:
207:
204:
199:
198:
187:
184:
183:
180:
174:
173:
170:
164:
163:
152:
139:
127:
107:
94:
83:
70:
56:
48:
21:
12:
11:
5:
3989:
3979:
3978:
3973:
3956:
3955:
3952:
3951:
3948:
3947:
3945:
3944:
3939:
3934:
3929:
3924:
3919:
3914:
3909:
3904:
3899:
3894:
3889:
3884:
3879:
3874:
3869:
3864:
3859:
3854:
3852:Hantzsch ester
3849:
3844:
3839:
3834:
3829:
3824:
3819:
3814:
3809:
3804:
3799:
3794:
3789:
3784:
3779:
3774:
3769:
3764:
3762:Banert cascade
3759:
3754:
3749:
3744:
3738:
3736:
3732:
3731:
3729:
3728:
3723:
3718:
3713:
3708:
3703:
3701:Prato reaction
3698:
3693:
3688:
3683:
3678:
3673:
3668:
3663:
3658:
3653:
3648:
3643:
3638:
3633:
3628:
3623:
3618:
3613:
3608:
3603:
3598:
3593:
3588:
3583:
3578:
3573:
3567:
3565:
3556:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3450:
3445:
3440:
3435:
3430:
3425:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3365:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3320:
3315:
3310:
3305:
3300:
3295:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3245:
3240:
3235:
3230:
3225:
3220:
3215:
3210:
3204:
3202:
3194:
3193:
3191:
3190:
3185:
3180:
3175:
3170:
3165:
3160:
3155:
3150:
3145:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3105:
3100:
3095:
3090:
3085:
3080:
3075:
3070:
3065:
3060:
3055:
3050:
3045:
3040:
3035:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2925:
2920:
2915:
2910:
2905:
2900:
2895:
2890:
2885:
2880:
2875:
2870:
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2795:
2793:Banert cascade
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2719:
2717:
2713:Rearrangement
2709:
2708:
2706:
2705:
2703:Zinin reaction
2700:
2695:
2690:
2685:
2680:
2675:
2673:Wacker process
2670:
2665:
2660:
2655:
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2448:Hydrogenolysis
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2398:Étard reaction
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2303:Bosch reaction
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2240:
2235:
2230:
2225:
2220:
2214:
2212:
2208:Organic redox
2204:
2203:
2201:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2150:
2145:
2140:
2135:
2129:
2127:
2121:
2120:
2118:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2082:
2077:
2072:
2067:
2062:
2057:
2052:
2047:
2042:
2040:Esterification
2037:
2032:
2027:
2022:
2017:
2011:
2009:
2001:
2000:
1997:
1996:
1994:
1993:
1988:
1983:
1978:
1973:
1968:
1963:
1958:
1953:
1948:
1943:
1938:
1933:
1928:
1923:
1918:
1913:
1908:
1903:
1898:
1893:
1887:
1885:
1881:
1880:
1878:
1877:
1872:
1867:
1862:
1857:
1852:
1847:
1841:
1839:
1830:
1829:
1824:
1819:
1817:Wurtz reaction
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1764:
1759:
1754:
1749:
1744:
1739:
1734:
1729:
1724:
1719:
1714:
1709:
1704:
1699:
1694:
1689:
1687:Prins reaction
1684:
1679:
1674:
1669:
1664:
1659:
1654:
1649:
1644:
1639:
1634:
1629:
1624:
1619:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1569:
1564:
1559:
1554:
1549:
1544:
1539:
1534:
1529:
1524:
1519:
1514:
1509:
1504:
1502:Hydrocyanation
1499:
1494:
1489:
1484:
1479:
1474:
1472:Henry reaction
1469:
1464:
1459:
1454:
1449:
1444:
1439:
1434:
1429:
1424:
1419:
1414:
1409:
1404:
1399:
1394:
1389:
1384:
1379:
1374:
1369:
1364:
1359:
1354:
1349:
1344:
1339:
1334:
1329:
1324:
1319:
1314:
1309:
1304:
1299:
1294:
1289:
1284:
1279:
1274:
1269:
1264:
1259:
1254:
1249:
1244:
1239:
1234:
1229:
1224:
1219:
1214:
1209:
1204:
1199:
1194:
1189:
1184:
1179:
1174:
1172:Aldol reaction
1169:
1164:
1159:
1153:
1151:
1146:Carbon-carbon
1143:
1142:
1131:
1130:
1125:
1123:Zaitsev's rule
1120:
1115:
1110:
1105:
1100:
1095:
1090:
1085:
1080:
1075:
1070:
1068:Steric effects
1065:
1060:
1055:
1050:
1045:
1040:
1035:
1030:
1025:
1020:
1015:
1010:
1005:
1000:
995:
990:
985:
980:
975:
970:
965:
960:
955:
950:
945:
940:
935:
930:
925:
920:
915:
910:
905:
900:
895:
890:
885:
880:
875:
870:
865:
860:
855:
850:
845:
840:
835:
830:
825:
820:
815:
810:
805:
800:
795:
790:
785:
780:
775:
770:
765:
760:
755:
749:
746:
745:
743:
742:
737:
732:
727:
722:
720:Redox reaction
717:
712:
707:
705:Polymerization
702:
697:
691:
688:
687:
679:
678:
671:
664:
656:
649:
648:
620:
592:
557:
546:(6): 612–619.
529:
499:
492:
456:
454:
451:
446:
443:
423:
422:
417:
410:
409:Other reagents
407:
396:
395:
391:
387:
383:
382:→ 3 RCHO + 3 H
379:
375:
371:
352:
349:
337:
334:
332:orange solid.
289:
286:
285:
280:
276:standard state
273:
270:
269:
266:
260:
259:
256:
252:
251:
248:
242:
241:
237:
233:
229:
225:
222:
217:
214:
213:
209:
208:
206:
205:
202:
194:
193:
192:
189:
188:
186:
185:
181:
178:
177:
175:
171:
168:
167:
159:
158:
157:
154:
153:
151:
150:
142:
140:
132:
129:
128:
126:
125:
117:
115:
109:
108:
106:
105:
97:
95:
88:
85:
84:
82:
81:
73:
71:
66:
63:
62:
58:
57:
54:
50:
49:
46:
40:
39:
35:
34:
9:
6:
4:
3:
2:
3988:
3977:
3974:
3972:
3969:
3968:
3966:
3943:
3940:
3938:
3935:
3933:
3930:
3928:
3925:
3923:
3920:
3918:
3915:
3913:
3910:
3908:
3905:
3903:
3900:
3898:
3895:
3893:
3890:
3888:
3885:
3883:
3880:
3878:
3875:
3873:
3870:
3868:
3865:
3863:
3862:Herz reaction
3860:
3858:
3855:
3853:
3850:
3848:
3845:
3843:
3840:
3838:
3835:
3833:
3830:
3828:
3825:
3823:
3820:
3818:
3815:
3813:
3810:
3808:
3805:
3803:
3800:
3798:
3795:
3793:
3790:
3788:
3785:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3739:
3737:
3733:
3727:
3724:
3722:
3719:
3717:
3714:
3712:
3709:
3707:
3704:
3702:
3699:
3697:
3694:
3692:
3689:
3687:
3684:
3682:
3679:
3677:
3674:
3672:
3669:
3667:
3664:
3662:
3659:
3657:
3654:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3614:
3612:
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3587:
3584:
3582:
3579:
3577:
3574:
3572:
3569:
3568:
3566:
3564:
3563:Cycloaddition
3560:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3426:
3424:
3421:
3419:
3416:
3414:
3411:
3409:
3408:Isay reaction
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3303:Cycloaddition
3301:
3299:
3296:
3294:
3291:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3244:
3241:
3239:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3205:
3203:
3201:
3198:Ring forming
3195:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3159:
3156:
3154:
3151:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3098:Rupe reaction
3096:
3094:
3091:
3089:
3086:
3084:
3081:
3079:
3076:
3074:
3071:
3069:
3066:
3064:
3061:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3034:
3031:
3029:
3026:
3024:
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2909:
2906:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2801:
2799:
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2726:
2724:
2721:
2720:
2718:
2716:
2710:
2704:
2701:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2664:
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2488:Ley oxidation
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2453:Hydroxylation
2451:
2449:
2446:
2444:
2443:Hydrogenation
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2378:DNA oxidation
2376:
2374:
2371:
2369:
2368:Deoxygenation
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2309:
2306:
2304:
2301:
2299:
2296:
2294:
2291:
2289:
2286:
2284:
2281:
2279:
2276:
2274:
2271:
2269:
2266:
2264:
2261:
2259:
2258:Aromatization
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2215:
2213:
2211:
2205:
2199:
2196:
2194:
2191:
2189:
2186:
2184:
2181:
2179:
2176:
2174:
2171:
2169:
2166:
2164:
2161:
2159:
2156:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2130:
2128:
2122:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2095:Reed reaction
2093:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2012:
2010:
2006:bond forming
2002:
1992:
1989:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1967:
1964:
1962:
1959:
1957:
1954:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1914:
1912:
1911:Cope reaction
1909:
1907:
1904:
1902:
1899:
1897:
1894:
1892:
1889:
1888:
1886:
1882:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1842:
1840:
1838:
1834:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1750:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1723:
1720:
1718:
1715:
1713:
1710:
1708:
1705:
1703:
1700:
1698:
1695:
1693:
1690:
1688:
1685:
1683:
1680:
1678:
1675:
1673:
1670:
1668:
1665:
1663:
1660:
1658:
1655:
1653:
1650:
1648:
1645:
1643:
1640:
1638:
1635:
1633:
1630:
1628:
1625:
1623:
1622:Nef synthesis
1620:
1618:
1615:
1613:
1610:
1608:
1605:
1603:
1600:
1598:
1597:Methylenation
1595:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1568:
1565:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1520:
1518:
1515:
1513:
1510:
1508:
1505:
1503:
1500:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1473:
1470:
1468:
1467:Heck reaction
1465:
1463:
1460:
1458:
1455:
1453:
1450:
1448:
1445:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1425:
1423:
1420:
1418:
1415:
1413:
1410:
1408:
1405:
1403:
1400:
1398:
1395:
1393:
1390:
1388:
1385:
1383:
1380:
1378:
1375:
1373:
1370:
1368:
1365:
1363:
1360:
1358:
1355:
1353:
1350:
1348:
1345:
1343:
1340:
1338:
1335:
1333:
1330:
1328:
1325:
1323:
1320:
1318:
1315:
1313:
1310:
1308:
1305:
1303:
1300:
1298:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1275:
1273:
1270:
1268:
1265:
1263:
1260:
1258:
1255:
1253:
1250:
1248:
1245:
1243:
1240:
1238:
1235:
1233:
1230:
1228:
1225:
1223:
1220:
1218:
1215:
1213:
1210:
1208:
1205:
1203:
1200:
1198:
1195:
1193:
1190:
1188:
1185:
1183:
1180:
1178:
1175:
1173:
1170:
1168:
1165:
1163:
1160:
1158:
1155:
1154:
1152:
1148:bond forming
1144:
1140:
1135:
1129:
1126:
1124:
1121:
1119:
1116:
1114:
1113:Y-aromaticity
1111:
1109:
1106:
1104:
1101:
1099:
1098:Walsh diagram
1096:
1094:
1091:
1089:
1086:
1084:
1083:Taft equation
1081:
1079:
1076:
1074:
1071:
1069:
1066:
1064:
1061:
1059:
1056:
1054:
1053:ÎŁ-aromaticity
1051:
1049:
1046:
1044:
1041:
1039:
1036:
1034:
1031:
1029:
1026:
1024:
1021:
1019:
1016:
1014:
1011:
1009:
1006:
1004:
1001:
999:
996:
994:
991:
989:
986:
984:
981:
979:
978:Marcus theory
976:
974:
971:
969:
966:
964:
961:
959:
956:
954:
953:HĂĽckel's rule
951:
949:
946:
944:
941:
939:
936:
934:
931:
929:
926:
924:
921:
919:
916:
914:
911:
909:
908:Evelyn effect
906:
904:
901:
899:
896:
894:
891:
889:
888:Electron-rich
886:
884:
881:
879:
876:
874:
871:
869:
866:
864:
861:
859:
856:
854:
851:
849:
846:
844:
841:
839:
836:
834:
831:
829:
826:
824:
821:
819:
816:
814:
811:
809:
806:
804:
803:Bema Hapothle
801:
799:
796:
794:
791:
789:
786:
784:
781:
779:
776:
774:
771:
769:
766:
764:
761:
759:
756:
754:
751:
750:
747:
741:
738:
736:
733:
731:
728:
726:
723:
721:
718:
716:
713:
711:
708:
706:
703:
701:
698:
696:
693:
692:
689:
685:
677:
672:
670:
665:
663:
658:
657:
654:
644:
640:
636:
633:
632:
624:
616:
612:
608:
605:
604:
603:J. Org. Chem.
596:
588:
584:
580:
576:
572:
568:
561:
553:
549:
545:
541:
533:
525:
521:
517:
513:
506:
504:
495:
489:
485:
481:
477:
470:
468:
466:
464:
462:
457:
450:
442:
440:
436:
432:
428:
427:Jones reagent
421:
418:
416:
413:
412:
406:
403:
401:
369:
368:
367:
364:
362:
358:
348:
345:
343:
333:
331:
327:
323:
319:
315:
311:
307:
303:
299:
295:
283:
277:
271:
267:
265:
262:
261:
258:Red crystals
257:
254:
253:
249:
247:
244:
243:
223:
220:
216:
215:
210:
201:
200:
197:
190:
176:
166:
165:
162:
155:
148:
144:
143:
141:
135:
131:
130:
123:
119:
118:
116:
114:
111:
110:
103:
99:
98:
96:
92:
87:
86:
79:
75:
74:
72:
69:
65:
64:
59:
51:
45:
41:
36:
32:
27:
19:
2903:Ene reaction
2263:Autoxidation
2124:Degradation
2015:Azo coupling
1792:Ugi reaction
1392:Ene reaction
1192:Alkynylation
1043:Polyfluorene
1038:Polar effect
903:Electrophile
818:Bredt's rule
788:Baird's rule
758:Alpha effect
634:
629:
623:
606:
601:
595:
570:
566:
560:
543:
539:
532:
515:
511:
475:
448:
424:
404:
397:
394:+ 4 pyridine
365:
354:
346:
339:
293:
292:
61:Identifiers
53:Other names
1402:Ethenolysis
1048:Ring strain
1018:Nucleophile
843:Clar's rule
783:Aromaticity
330:hygroscopic
268:1.565 g/cm
255:Appearance
212:Properties
3965:Categories
3686:Ozonolysis
3213:Annulation
2563:Ozonolysis
682:Topics in
493:0471936235
453:References
437:. PCC and
378:(pyridine)
374:OH + 2 CrO
246:Molar mass
113:ChemSpider
89:3D model (
78:26412-88-4
68:CAS Number
44:IUPAC name
3200:reactions
2715:reactions
2210:reactions
2126:reactions
2008:reactions
1150:reactions
357:aldehydes
351:Reactions
318:aldehydes
1093:Vinylogy
763:Annulene
710:Reagents
587:18102959
302:pyridine
753:A value
435:ketones
361:ketones
326:ketones
308:. This
264:Density
240:
134:PubChem
585:
490:
386:O + Cr
196:SMILES
38:Names
518:: 5.
370:3 RCH
300:with
161:InChI
147:88565
122:79908
91:JSmol
583:PMID
488:ISBN
429:and
359:and
320:and
639:doi
611:doi
575:doi
548:doi
520:doi
480:doi
304:in
232:CrN
137:CID
3967::
607:35
581:.
571:70
569:.
544:81
542:.
516:52
514:.
502:^
486:.
478:.
460:^
230:10
226:10
675:e
668:t
661:v
645:.
641::
635:9
617:.
613::
589:.
577::
554:.
550::
526:.
522::
496:.
482::
392:3
390:O
388:2
384:2
380:2
376:3
372:2
238:3
236:O
234:2
228:H
224:C
93:)
20:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
