454:
302:
503:
316:
381:
790:
570:
265:
ozone at different rates, one can choose an indicator whose own oxidation rate is intermediate between them, and therefore stop the reaction when only the most susceptible alkene in the substrate has reacted. Otherwise, the presence of unreacted ozone in solution (seeing its blue color) or in the bubbles (via iodide detection) only indicates when all alkenes have reacted.
532:, who discovered ozone in 1840, also did the first ozonolysis: in 1845, he reported that ethylene reacts with ozone â after the reaction, neither the smell of ozone nor the smell of ethylene was perceivable. The ozonolysis of alkenes is sometimes referred to as "Harries ozonolysis", because some attribute this reaction to
264:
can be added to the reaction mixture. Ozone reacts with this indicator more slowly than with the intended ozonolysis target. The ozonolysis of the indicator, which causes a noticeable color change, only occurs once the desired target has been consumed. If the substrate has two alkenes that react with
251:
at â78 °C (â108 °F; 195 K) until the solution takes on a characteristic blue color, which is due to unreacted ozone. Industry however recommends temperatures near â20 °C (â4 °F; 253 K). This color change indicates complete consumption of the alkene. Alternatively,
252:
various other reagents can be used as indicators of this endpoint by detecting the presence of ozone. If ozonolysis is performed by introducing a stream of ozone-enriched oxygen through the reaction mixture, the effluent gas can be directed through a
536:. Before the advent of modern spectroscopic techniques, the ozonolysis was an important method for determining the structure of organic molecules. Chemists would ozonize an unknown alkene to yield smaller and more readily identifiable fragments.
102:) groups, such as aldehydes, ketones, and carboxylic acids. The reaction is predominantly applied to alkenes, but alkynes and azo compounds are also susceptible to cleavage. The outcome of the reaction depends on the type of multiple bond being
520:
reacts with carbonyl oxides, the label ends up exclusively in the ether linkage of the ozonide. There is still dispute over whether the molozonide collapses via a concerted or radical process; this may also exhibit a substrate dependence.
781:
A number of drugs and their intermediates have been produced by ozonolysis. The use of ozone in the pharmaceutical industry is difficult to discern owing to confidentiality considerations.
2592:
560:. A reducing agent is not needed for these reactions. The mechanism is unknown. If the reaction is performed in the presence of water, the anhydride hydrolyzes to give two
4807:
1601:
Caron, Stéphane; Dugger, Robert W.; Ruggeri, Sally Gut; Ragan, John A.; Ripin, David H. Brown (2006). "Large-Scale
Oxidations in the Pharmaceutical Industry".
340:, can also be oxidized by ozone. It has been proposed that small amounts of acid may be generated during the reaction from oxidation of the solvent, so
3923:
3868:
4636:
485:) in a retro-1,3-dipolar cycloaddition. The oxide and aldehyde or ketone react again in a 1,3-dipolar cycloaddition, producing a relatively stable
3978:
4128:
2762:
4857:
1358:
218:
4631:
2457:
490:
1131:
Veysoglu, Tarik; Mitscher, Lester A.; Swayze, John K. (1980). "A Convenient Method for the
Control of Selective Ozonizations of Olefins".
3733:
1654:
4303:
3503:
2247:
1105:
4468:
4398:
4378:
3873:
3040:
2502:
2921:
2477:
1690:
4223:
4701:
4651:
3055:
4158:
4797:
4606:
4263:
4243:
4203:
3010:
1953:
1552:
1328:
962:
1568:
Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids".
4956:
4792:
4722:
4621:
4278:
4133:
3763:
3608:
3218:
2845:
2622:
1238:
Claus, Ronald E.; Schreiber, Stuart L. (1986). "Ozonolytic
Cleavage of Cyclohexene to Terminally Differentiated Products".
4872:
4656:
3968:
3458:
3133:
72:
3678:
4867:
4581:
4443:
4233:
4198:
1048:
607:
The main use of ozonolysis is for the conversion of unsaturated fatty acids to value-added derivatives. Ozonolysis of
4757:
4696:
4228:
4143:
4113:
4093:
3958:
3953:
3328:
3253:
2896:
2850:
2717:
1978:
1439:
1293:
502:
268:
After completing the addition, a reagent is then added to convert the intermediate ozonide to a carbonyl derivative.
203:
46:
260:, which can easily be observed by its violet color. For closer control of the reaction itself, an indicator such as
4951:
4862:
4822:
4772:
4448:
4248:
3998:
3928:
2417:
1988:
4063:
2956:
2677:
529:
387:
By controlling the reaction/workup conditions, unsymmetrical products can be generated from symmetrical alkenes:
4616:
4458:
4328:
4323:
4138:
3613:
3523:
3113:
3045:
2936:
2512:
2267:
2192:
1647:
4373:
4902:
4787:
4686:
4626:
4273:
4068:
4028:
4003:
3913:
3373:
2407:
2337:
1973:
1903:
1585:
1455:
Cremer, D.; Crehuet, R.; Anglada, J. (2001). "The
Ozonolysis of Acetylene â A Quantum Chemical Investigation".
1115:
3493:
1069:
Van Ornum, Scott G.; Champeau, Robin M.; Pariza, Richard (2006). "Ozonolysis
Applications in Drug Synthesis".
853:
if the polymer is exposed to light. To minimize this problem, many polyolefin-based products are treated with
4892:
4478:
4368:
3988:
3713:
3498:
3443:
3288:
3248:
3080:
2835:
2552:
2402:
1204:
914:
4852:
4413:
3858:
4887:
4802:
4777:
4752:
4737:
4661:
4576:
4473:
4433:
4298:
4253:
4018:
3563:
3548:
3413:
3203:
2871:
2627:
2307:
2282:
2252:
1843:
864:
where active chemical species attack products of a susceptible material. The rubber product must be under
4837:
4782:
4727:
4438:
4358:
4258:
3973:
3938:
3783:
3673:
3388:
3383:
3208:
3168:
3065:
2876:
2840:
2692:
2682:
2537:
2397:
2257:
2207:
2202:
2177:
2137:
2083:
1848:
1838:
1813:
1267:
952:
4812:
4513:
4318:
3753:
3638:
3318:
3293:
3233:
3090:
2825:
2532:
2312:
2277:
2182:
1873:
1808:
1640:
211:
4103:
2367:
4912:
4817:
4671:
4551:
4523:
4493:
4408:
4338:
4293:
4268:
4188:
4088:
4048:
3743:
3363:
3353:
3278:
2802:
2662:
2657:
2637:
2322:
2119:
2098:
2058:
1983:
861:
470:
1803:
1199:
1158:
Schwartz, Chris; Raible, J.; Mott, K.; Dussault, P. H. (2006). "Fragmentation of
Carbonyl Oxides by
880:. Other means of prevention include replacing susceptible rubbers with resistant elastomers such as
4877:
4767:
4747:
4611:
4453:
4363:
4333:
4313:
4208:
4163:
3993:
3903:
3833:
3718:
3708:
3538:
3095:
3035:
3000:
2807:
2787:
2747:
2522:
2392:
2357:
2317:
2068:
1908:
1898:
1828:
1397:"The History of Ozone Part III, C. D. Harries and the Introduction of Ozone into Organic Chemistry"
4343:
4961:
4847:
4706:
4556:
4498:
4423:
4403:
4123:
4073:
3933:
3898:
3838:
3768:
3323:
3070:
3050:
2782:
2702:
2597:
2557:
2527:
2462:
2347:
2332:
2242:
2232:
1893:
1818:
1773:
1344:
Geletneky, C.; Berger, S. (1998). "The
Mechanism of Ozonolysis Revisited by O-NMR Spectroscopy".
256:
solution. When the solution has stopped absorbing ozone, the excess ozone oxidizes the iodide to
2108:
4586:
4308:
4058:
4038:
4013:
3963:
3878:
3853:
3808:
3778:
3758:
3728:
3693:
3648:
3623:
3598:
3483:
3408:
3188:
2881:
2817:
2617:
2342:
2262:
1948:
1923:
1700:
1695:
1401:
132:
91:
30:
4922:
4508:
4463:
4178:
4148:
4118:
4053:
4033:
3948:
3943:
3908:
3863:
3848:
3843:
3823:
3813:
3748:
3738:
3668:
3618:
3138:
2941:
2517:
2472:
2302:
2292:
2038:
1963:
1758:
1720:
1040:
1034:
705:. The conversion entails ozonolysis, which selectively cleaves the C=C bond in erucic acid:
1968:
1373:
4691:
4641:
4591:
4571:
4561:
4418:
4393:
4108:
4098:
3983:
3798:
3793:
3723:
3508:
3308:
3268:
3198:
3163:
3118:
3085:
2951:
2926:
2906:
2727:
2687:
2647:
2612:
2542:
2297:
2167:
2142:
1680:
1212:
849:. Ozonolysis produces surface ketone groups that can cause further gradual degradation via
474:
8:
4897:
4882:
4528:
4503:
4488:
4483:
4213:
4168:
4153:
4043:
4023:
3918:
3803:
3788:
3633:
3578:
3568:
3533:
3298:
3173:
3148:
3060:
2916:
2901:
2886:
2707:
2652:
2422:
2272:
2217:
2088:
2003:
1863:
1788:
909:
272:
232:
107:
4907:
3558:
2742:
1933:
1216:
4646:
4596:
4566:
4428:
4218:
4008:
3893:
3828:
3818:
3583:
3513:
3478:
3473:
3453:
3448:
3393:
3303:
3153:
3015:
3005:
2911:
2697:
2642:
2572:
2492:
2387:
2287:
2222:
2147:
1993:
1858:
1793:
1778:
1346:
396:
295:
279:
453:
4383:
3703:
3588:
3553:
3518:
3463:
3418:
3333:
3313:
3263:
3258:
3228:
3213:
3123:
3030:
2966:
2931:
2757:
2632:
2507:
2432:
2412:
2327:
2162:
2157:
2103:
2013:
1918:
1878:
1833:
1715:
1710:
1675:
1618:
1581:
1548:
1501:
1473:
1457:
1435:
1324:
1180:
1111:
1086:
1044:
1011:
983:
958:
926:
900:
The use of ozone in the pharmaceutical industry is limited by safety considerations.
868:
for crack growth to occur. Ozone cracking was once commonly seen in the sidewalls of
865:
842:
694:
513:
473:. Next, the molozonide reverts to its corresponding carbonyl oxide (also called the
309:
269:
60:
3378:
4917:
4762:
4732:
4676:
4601:
4533:
4288:
4238:
4083:
3888:
3663:
3658:
3603:
3593:
3368:
3178:
3158:
3128:
3025:
2961:
2946:
2777:
2732:
2722:
2712:
2607:
2587:
2582:
2567:
2562:
2442:
2437:
2377:
2362:
2352:
2197:
2187:
2053:
2043:
1943:
1938:
1913:
1853:
1705:
1664:
1610:
1573:
1540:
1510:
1465:
1410:
1354:
1316:
1275:
1247:
1220:
1172:
1140:
1078:
921:
850:
414:
404:
330:
291:
253:
68:
2033:
1577:
4827:
4518:
4353:
4348:
3643:
3628:
3573:
3528:
3488:
3438:
3403:
3398:
3343:
3338:
3273:
3223:
3143:
2971:
2855:
2830:
2792:
2767:
2752:
2737:
2672:
2547:
2497:
2487:
2467:
2427:
2237:
2227:
2212:
2008:
1928:
1798:
1768:
1753:
1748:
881:
561:
372:
357:
349:
345:
244:
1492:
1006:
978:
4832:
4742:
4681:
3773:
3683:
3653:
3428:
3283:
3020:
2797:
2667:
2482:
2452:
2152:
2048:
1823:
1685:
1359:
10.1002/(SICI)1099-0690(199808)1998:8<1625::AID-EJOC1625>3.0.CO;2-L
873:
846:
834:
826:
810:
794:
690:
549:
462:
352:
is often used as a 1:1 cosolvent to facilitate timely cleavage of the ozonide.
301:
247:. In a typical procedure, ozone is bubbled through a solution of the alkene in
1632:
4945:
4842:
4543:
4388:
4283:
4078:
3468:
3433:
3423:
3358:
3348:
3238:
3075:
2891:
2602:
2577:
2447:
2093:
2078:
2063:
1958:
1888:
1868:
1783:
1544:
1514:
1320:
1251:
838:
616:
422:
261:
76:
3883:
3243:
2995:
2772:
2372:
2172:
2023:
2018:
1883:
1738:
1622:
1477:
1415:
1396:
1279:
1184:
1090:
612:
584:
533:
517:
353:
315:
2382:
2028:
1998:
1763:
1378:
Bericht ĂŒber die
Verhandlungen der Naturforschenden Gesellschaft in Basel
1144:
948:
877:
854:
806:
592:
789:
4193:
1224:
1164:
830:
802:
608:
478:
466:
361:
1614:
1469:
1176:
1082:
702:
698:
1535:
Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic".
569:
380:
275:
conditions are far more commonly used than oxidative conditions.
2073:
1743:
814:
553:
341:
283:
248:
236:
103:
95:
1733:
1200:"Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol"
1198:
Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R. (2007).
486:
368:
323:
954:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
801:
Ozonolysis has been used to characterize the structure of some
557:
545:
408:
334:
257:
240:
1493:"Asymmetric Syntheses using the SAMP-/RAMP-Hydrozone Method: (
1007:"Dialkyl Mesoxalates by Ozonolysis of Dialkyl Benzalmalonates"
1371:
946:
889:
430:
337:
80:
957:(6th ed.), New York: Wiley-Interscience, p. 1036,
917:â an alternative system using periodate and osmium tetroxide
1110:(2nd ed.). San Diego, CA: Academic Press. p. 35.
885:
869:
392:
287:
1157:
1567:
1311:
Li, Jie Jack (2006). "Criegee mechanism of ozonolysis".
1600:
1068:
1036:
Experimental
Organic Chemistry: Principles and Practice
1130:
1162:-Oxides: An Improved Approach to Alkene Ozonolysis".
784:
4808:
ErlenmeyerâPlöchl azlactone and amino-acid synthesis
1454:
1374:"Ueber das Verhalten des Ozons zum oelbildenden Gas"
1033:
Harwood, Laurence M.; Moody, Christopher J. (1989).
298:produces alcohols. (R group can also be hydrogens)
465:in 1953, the alkene and ozone form an intermediate
1197:
1039:(Illustrated ed.). Wiley-Blackwell. pp.
3869:Divinylcyclopropane-cycloheptadiene rearrangement
1394:
1026:
829:where traces of the gas in an atmosphere degrade
4943:
461:In the generally accepted mechanism proposed by
294:produces aldehydes or ketones. While the use of
1662:
1491:Enders, Dieter; Kipphardt, Helmut; Fey, Peter.
1343:
1265:Criegee, R. (1975). "Mechanism of Ozonolysis".
4129:Thermal rearrangement of aromatic hydrocarbons
2763:Thermal rearrangement of aromatic hydrocarbons
1570:Ullmann's Encyclopedia of Industrial Chemistry
1537:Ullmann's Encyclopedia of Industrial Chemistry
1490:
1237:
976:
825:Ozonolysis can be a serious problem, known as
444:N, gives a methyl ester and a dimethyl acetal.
4858:Lectka enantioselective beta-lactam synthesis
2118:
1648:
1434:. Vol. 2. New York, NY: Academic Press.
876:, but is now rare owing to the use of modern
872:, where it could expand to cause a dangerous
16:Cleavage of C=C, CâĄC, or N=N bonds with ozone
4637:Inverse electron-demand DielsâAlder reaction
2458:Heterogeneous metal catalyzed cross-coupling
1534:
1032:
314:
300:
3979:Lobry de BruynâVan Ekenstein transformation
1365:
1004:
556:product, not complete fragmentation as for
231:Alkenes can be oxidized with ozone to form
1655:
1641:
4469:Petrenko-Kritschenko piperidone synthesis
3924:FritschâButtenbergâWiechell rearrangement
1414:
1231:
1191:
113:Detailed procedures have been reported.
4632:Intramolecular DielsâAlder cycloaddition
1388:
788:
539:
512:Evidence for this mechanism is found in
452:
143:
116:
1561:
1264:
977:Bailey, P. S.; Erickson, R. E. (1973).
407:(DMS) gives an aldehyde and a dimethyl
4944:
4652:Metal-centered cycloaddition reactions
4304:DebusâRadziszewski imidazole synthesis
2248:BodrouxâChichibabin aldehyde synthesis
1429:
1372:Christian Friedrich Schönbein (1847).
4798:Diazoalkane 1,3-dipolar cycloaddition
4702:Vinylcyclopropane (5+2) cycloaddition
4607:Diazoalkane 1,3-dipolar cycloaddition
4379:HurdâMori 1,2,3-thiadiazole synthesis
3874:DowdâBeckwith ring-expansion reaction
3041:HurdâMori 1,2,3-thiadiazole synthesis
2117:
1954:LFER solvent coefficients (data page)
1636:
1064:
1062:
1060:
506:The reaction mechanism of ozonolysis.
448:
3609:Sharpless asymmetric dihydroxylation
2846:Methoxymethylenetriphenylphosphorane
1107:Natural Products: A Laboratory Guide
1103:
805:. Early experiments showed that the
3734:AllenâMillarâTrippett rearrangement
1430:Bailey, P. S. (1982). "Chapter 2".
578:
457:Carbonyl oxide (Criegee zwitterion)
13:
4873:Nitrone-olefin (3+2) cycloaddition
4868:Niementowski quinazoline synthesis
4657:Nitrone-olefin (3+2) cycloaddition
4582:Azide-alkyne Huisgen cycloaddition
4444:Niementowski quinazoline synthesis
4199:Azide-alkyne Huisgen cycloaddition
3504:MeerweinâPonndorfâVerley reduction
3056:LeimgruberâBatcho indole synthesis
1310:
1057:
785:Ozonolysis as an analytical method
591:) are susceptible to ozonolysis.
568:
501:
329:produce aldehydes directly. Other
14:
4973:
4697:Trimethylenemethane cycloaddition
4399:JohnsonâCoreyâChaykovsky reaction
4264:CadoganâSundberg indole synthesis
4244:BohlmannâRahtz pyridine synthesis
4204:BaeyerâEmmerling indole synthesis
3011:CadoganâSundberg indole synthesis
2503:JohnsonâCoreyâChaykovsky reaction
1005:Tietze, L. F.; Bratz, M. (1998).
4793:CookâHeilbron thiazole synthesis
4622:Hexadehydro DielsâAlder reaction
4449:Niementowski quinoline synthesis
4279:CookâHeilbron thiazole synthesis
4224:BischlerâMöhlau indole synthesis
4134:TiffeneauâDemjanov rearrangement
3764:BakerâVenkataraman rearrangement
2922:HornerâWadsworthâEmmons reaction
2593:Mizoroki-Heck vs. Reductive Heck
2478:HornerâWadsworthâEmmons reaction
1989:Neighbouring group participation
379:
367:An example is the ozonolysis of
360:are produced from ozonolysis of
312:can produce carboxylic acids.
4329:Fiesselmann thiophene synthesis
4159:WestphalenâLettrĂ© rearrangement
4139:Vinylcyclopropane rearrangement
3969:KornblumâDeLaMare rearrangement
3614:Epoxidation of allylic alcohols
3524:Noyori asymmetric hydrogenation
3459:KornblumâDeLaMare rearrangement
3134:GallagherâHollander degradation
1594:
1528:
1484:
1448:
1423:
1337:
1304:
1286:
1258:
697:that is used to make specialty
602:
4788:Chichibabin pyridine synthesis
4274:Chichibabin pyridine synthesis
4234:BlumâIttah aziridine synthesis
4069:Ring expansion and contraction
2338:Cross dehydrogenative coupling
1432:Ozonation in Organic Chemistry
1315:. Springer. pp. 173â174.
1151:
1124:
1097:
998:
970:
940:
689:Erucic acid is a precursor to
1:
4758:BischlerâNapieralski reaction
4716:Heterocycle forming reactions
4369:Hemetsberger indole synthesis
4229:BischlerâNapieralski reaction
4144:WagnerâMeerwein rearrangement
4114:SommeletâHauser rearrangement
4094:SeyferthâGilbert homologation
3959:IrelandâClaisen rearrangement
3954:HofmannâMartius rearrangement
3714:2,3-sigmatropic rearrangement
3329:CoreyâWinter olefin synthesis
3254:BartonâMcCombie deoxygenation
2897:CoreyâWinter olefin synthesis
2851:SeyferthâGilbert homologation
2718:SeyferthâGilbert homologation
1578:10.1002/14356007.a10_245.pub2
933:
820:
530:Christian Friedrich Schönbein
4863:LehmstedtâTanasescu reaction
4823:GabrielâColman rearrangement
4778:Bucherer carbazole synthesis
4773:BorscheâDrechsel cyclization
4753:Bernthsen acridine synthesis
4738:Bamberger triazine synthesis
4723:AlgarâFlynnâOyamada reaction
4434:Nazarov cyclization reaction
4299:De Kimpe aziridine synthesis
4254:Bucherer carbazole synthesis
4249:BorscheâDrechsel cyclization
4019:Nazarov cyclization reaction
3999:MeyerâSchuster rearrangement
3929:GabrielâColman rearrangement
3679:WolffensteinâBöters reaction
3564:Reduction of nitro compounds
3414:Grundmann aldehyde synthesis
3219:AlgarâFlynnâOyamada reaction
2628:Olefin conversion technology
2623:NozakiâHiyamaâKishi reaction
2418:GabrielâColman rearrangement
2308:Claisen-Schmidt condensation
2253:Bouveault aldehyde synthesis
860:Ozone cracking is a form of
204:ozonolysis-criegee-mechanism
47:ozonolysis-criegee-mechanism
7:
4957:Organic oxidation reactions
4838:Hantzsch pyridine synthesis
4617:Enoneâalkene cycloadditions
4439:Nenitzescu indole synthesis
4359:Hantzsch pyridine synthesis
4324:FerrarioâAckermann reaction
3974:Kowalski ester homologation
3939:Halogen dance rearrangement
3784:Benzilic acid rearrangement
3209:Akabori amino-acid reaction
3169:Von Braun amide degradation
3114:BarbierâWieland degradation
3066:Nenitzescu indole synthesis
3046:KharaschâSosnovsky reaction
2937:JuliaâKocienski olefination
2841:Kowalski ester homologation
2538:Kowalski ester homologation
2513:JuliaâKocienski olefination
2268:CadiotâChodkiewicz coupling
2193:Aza-BaylisâHillman reaction
2138:Acetoacetic ester synthesis
1849:Dynamic binding (chemistry)
1839:Conrotatory and disrotatory
1814:Charge remote fragmentation
1497:)-(+)-4-Methyl-3-heptanone"
1268:Angew. Chem. Int. Ed. Engl.
903:
10:
4978:
4903:RobinsonâGabriel synthesis
4853:Kröhnke pyridine synthesis
4687:Retro-DielsâAlder reaction
4627:Imine DielsâAlder reaction
4414:Kröhnke pyridine synthesis
4029:NewmanâKwart rearrangement
4004:MislowâEvans rearrangement
3914:FischerâHepp rearrangement
3859:Di-Ï-methane rearrangement
3639:Stephen aldehyde synthesis
3374:EschweilerâClarke reaction
3091:Williamson ether synthesis
2408:FujiwaraâMoritani reaction
2313:Combes quinoline synthesis
2278:Carbonyl olefin metathesis
1979:More O'FerrallâJencks plot
1904:GrunwaldâWinstein equation
1874:Electron-withdrawing group
1809:Catalytic resonance theory
1523:, vol. 8, p. 403
1395:Mordecai B. Rubin (2003).
1021:, vol. 9, p. 314
993:, vol. 5, p. 489
929:alternative to ozonolysis.
583:Although rarely examined,
524:
481:) and aldehyde or ketone (
169:Typically reducing agents
4913:Urech hydantoin synthesis
4893:PomeranzâFritsch reaction
4818:Fischer oxazole synthesis
4715:
4552:1,3-Dipolar cycloaddition
4542:
4524:Urech hydantoin synthesis
4494:Reissert indole synthesis
4479:PomeranzâFritsch reaction
4409:Knorr quinoline synthesis
4339:Fischer oxazole synthesis
4269:Camps quinoline synthesis
4189:1,3-Dipolar cycloaddition
4177:
4089:Semipinacol rearrangement
4064:RambergâBĂ€cklund reaction
4049:Piancatelli rearrangement
3989:McFadyenâStevens reaction
3744:Alpha-ketol rearrangement
3692:
3499:McFadyenâStevens reaction
3444:KilianiâFischer synthesis
3364:Elbs persulfate oxidation
3289:BouveaultâBlanc reduction
3249:BaeyerâVilliger oxidation
3187:
3104:
3081:SchottenâBaumann reaction
2984:
2957:RambergâBĂ€cklund reaction
2864:
2836:KilianiâFischer synthesis
2816:
2678:RambergâBĂ€cklund reaction
2663:Pinacol coupling reaction
2658:Piancatelli rearrangement
2553:LiebeskindâSrogl coupling
2403:FujimotoâBelleau reaction
2126:
2120:List of organic reactions
1984:Negative hyperconjugation
1729:
1671:
915:LemieuxâJohnson oxidation
895:
862:stress corrosion cracking
611:is an important route to
489:intermediate, known as a
471:1,3-dipolar cycloaddition
225:
199:Organic Chemistry Portal
193:
182:
173:
166:
154:
147:
138:
123:
53:
42:Organic Chemistry Portal
36:
21:
4888:PictetâSpengler reaction
4803:EinhornâBrunner reaction
4768:Boger pyridine synthesis
4662:Oxo-DielsâAlder reaction
4577:Aza-DielsâAlder reaction
4474:PictetâSpengler reaction
4374:HofmannâLöffler reaction
4364:Hegedus indole synthesis
4334:Fischer indole synthesis
4209:Bartoli indole synthesis
4164:Willgerodt rearrangement
3994:McLafferty rearrangement
3904:Ferrier carbocyclization
3719:2,3-Wittig rearrangement
3709:1,2-Wittig rearrangement
3549:ParikhâDoering oxidation
3539:Oxygen rebound mechanism
3204:AdkinsâPeterson reaction
3096:Yamaguchi esterification
3036:Hegedus indole synthesis
3001:Bartoli indole synthesis
2872:BamfordâStevens reaction
2788:Weinreb ketone synthesis
2748:Stork enamine alkylation
2523:Knoevenagel condensation
2393:Ferrier carbocyclization
2283:CastroâStephens coupling
1909:Hammett acidity function
1899:Free-energy relationship
1844:CurtinâHammett principle
1829:Conformational isomerism
1545:10.1002/14356007.a08_523
1515:10.15227/orgsyn.065.0183
1321:10.1007/3-540-30031-7_77
1298:Organic Chemistry Portal
1252:10.15227/orgsyn.064.0150
364:on an industrial scale.
4952:Organic redox reactions
4848:Knorr pyrrole synthesis
4783:BuchererâBergs reaction
4728:AllanâRobinson reaction
4707:Wagner-Jauregg reaction
4499:Ring-closing metathesis
4424:Larock indole synthesis
4404:Knorr pyrrole synthesis
4259:BuchererâBergs reaction
4124:Stieglitz rearrangement
4104:SkattebĂžl rearrangement
4074:Ring-closing metathesis
3934:Group transfer reaction
3899:Favorskii rearrangement
3839:Cornforth rearrangement
3769:Bamberger rearrangement
3674:WolffâKishner reduction
3494:MarkĂłâLam deoxygenation
3389:FlemingâTamao oxidation
3384:FischerâTropsch process
3071:Oxymercuration reaction
3051:Knorr pyrrole synthesis
2877:BartonâKellogg reaction
2783:Wagner-Jauregg reaction
2703:Ring-closing metathesis
2693:ReimerâTiemann reaction
2683:RauhutâCurrier reaction
2598:Nef isocyanide reaction
2558:Malonic ester synthesis
2528:Knorr pyrrole synthesis
2463:High dilution principle
2398:FriedelâCrafts reaction
2333:Cross-coupling reaction
2258:BuchererâBergs reaction
2243:Blanc chloromethylation
2233:Blaise ketone synthesis
2208:BaylisâHillman reaction
2203:BartonâKellogg reaction
2178:AllanâRobinson reaction
2084:WoodwardâHoffmann rules
1819:Charge-transfer complex
4813:FeistâBenary synthesis
4587:Bradsher cycloaddition
4557:4+4 Photocycloaddition
4514:SimmonsâSmith reaction
4459:PaternĂČâBĂŒchi reaction
4319:FeistâBenary synthesis
4309:Dieckmann condensation
4059:Pummerer rearrangement
4039:Oxy-Cope rearrangement
4014:Myers allene synthesis
3964:Jacobsen rearrangement
3879:Electrocyclic reaction
3854:Demjanov rearrangement
3809:Buchner ring expansion
3779:Beckmann rearrangement
3759:Aza-Cope rearrangement
3754:ArndtâEistert reaction
3729:Alkyne zipper reaction
3649:Transfer hydrogenation
3624:Sharpless oxyamination
3599:Selenoxide elimination
3484:Lombardo methylenation
3409:Griesbaum coozonolysis
3319:CoreyâItsuno reduction
3294:BoylandâSims oxidation
3234:AngeliâRimini reaction
2882:Boord olefin synthesis
2826:ArndtâEistert reaction
2818:Homologation reactions
2618:Nitro-Mannich reaction
2533:KolbeâSchmitt reaction
2343:Cross-coupling partner
2263:Buchner ring expansion
2183:ArndtâEistert reaction
1949:Kinetic isotope effect
1696:Rearrangement reaction
1416:10.1002/hlca.200390111
1294:"Ozonolysis mechanism"
1280:10.1002/anie.197507451
1104:Ikan, Raphael (1991).
798:
573:
507:
458:
319:
305:
133:Organic redox reaction
31:Organic redox reaction
4672:PausonâKhand reaction
4509:Sharpless epoxidation
4464:Pechmann condensation
4344:FriedlÀnder synthesis
4294:DavisâBeirut reaction
4149:Wallach rearrangement
4119:Stevens rearrangement
4054:Pinacol rearrangement
4034:Overman rearrangement
3949:Hofmann rearrangement
3944:Hayashi rearrangement
3909:Ferrier rearrangement
3864:Dimroth rearrangement
3849:Curtius rearrangement
3844:Criegee rearrangement
3824:Claisen rearrangement
3814:Carroll rearrangement
3749:Amadori rearrangement
3739:Allylic rearrangement
3619:Sharpless epoxidation
3354:DessâMartin oxidation
3279:BohnâSchmidt reaction
3139:Hofmann rearrangement
2942:Kauffmann olefination
2865:Olefination reactions
2803:WurtzâFittig reaction
2638:PalladiumâNHC complex
2518:Kauffmann olefination
2473:Homologation reaction
2323:CoreyâHouse synthesis
2303:Claisen rearrangement
2099:YukawaâTsuno equation
2059:SwainâLupton equation
2039:Spherical aromaticity
1974:MöbiusâHĂŒckel concept
1759:Aromatic ring current
1721:Substitution reaction
792:
572:
540:Ozonolysis of alkynes
534:Carl Dietrich Harries
505:
456:
344:is sometimes used to
318:
304:
117:Ozonolysis of alkenes
4878:PaalâKnorr synthesis
4748:BartonâZard reaction
4692:Staudinger synthesis
4642:Ketene cycloaddition
4612:DielsâAlder reaction
4592:Cheletropic reaction
4572:Alkyne trimerisation
4454:PaalâKnorr synthesis
4419:Kulinkovich reaction
4394:Jacobsen epoxidation
4314:DielsâAlder reaction
4109:Smiles rearrangement
4099:Sigmatropic reaction
3984:Lossen rearrangement
3834:CoreyâFuchs reaction
3799:Boekelheide reaction
3794:Bergmann degradation
3724:Achmatowicz reaction
3509:Methionine sulfoxide
3309:Clemmensen reduction
3269:Bergmann degradation
3199:Acyloin condensation
3164:Strecker degradation
3119:Bergmann degradation
3086:Ullmann condensation
2952:Peterson olefination
2927:Hydrazone iodination
2907:Elimination reaction
2808:ZinckeâSuhl reaction
2728:Sonogashira coupling
2688:Reformatsky reaction
2648:Peterson olefination
2613:Nierenstein reaction
2543:Kulinkovich reaction
2358:DielsâAlder reaction
2318:CoreyâFuchs reaction
2298:Claisen condensation
2168:Alkyne trimerisation
2143:Acyloin condensation
2109:ÎŁ-bishomoaromaticity
2069:ThorpeâIngold effect
1681:Elimination reaction
1145:10.1055/s-1980-29214
475:Criegee intermediate
4898:Prilezhaev reaction
4883:Pellizzari reaction
4562:(4+3) cycloaddition
4529:Van Leusen reaction
4504:Robinson annulation
4489:Pschorr cyclization
4484:Prilezhaev reaction
4214:Bergman cyclization
4169:Wolff rearrangement
4154:Weerman degradation
4044:Pericyclic reaction
4024:Neber rearrangement
3919:Fries rearrangement
3804:Brook rearrangement
3789:Bergman cyclization
3634:Staudinger reaction
3579:Rosenmund reduction
3569:Reductive amination
3534:Oppenauer oxidation
3324:CoreyâKim oxidation
3299:Cannizzaro reaction
3174:Weerman degradation
3149:Isosaccharinic acid
3061:Mukaiyama hydration
2917:Hofmann elimination
2902:Dehydrohalogenation
2887:Chugaev elimination
2708:Robinson annulation
2653:Pfitzinger reaction
2423:Gattermann reaction
2368:WulffâDötz reaction
2348:DakinâWest reaction
2273:Carbonyl allylation
2218:Bergman cyclization
2004:Kennedy J. P. Orton
1924:Hammond's postulate
1894:FlippinâLodge angle
1864:Electromeric effect
1789:Beta-silicon effect
1774:BakerâNathan effect
1217:2007JChEd..84.1979B
947:Smith, Michael B.;
910:Polymer degradation
615:. The coproduct is
548:generally gives an
516:. When O-labelled
4647:McCormack reaction
4597:Conia-ene reaction
4429:Madelung synthesis
4219:Biginelli reaction
4009:Mumm rearrangement
3894:Favorskii reaction
3829:Cope rearrangement
3819:Chan rearrangement
3584:Rubottom oxidation
3514:Miyaura borylation
3479:Lipid peroxidation
3474:Lindgren oxidation
3454:Kornblum oxidation
3449:Kolbe electrolysis
3394:Fukuyama reduction
3304:Carbonyl reduction
3154:Marker degradation
3016:Diazonium compound
3006:Boudouard reaction
2985:Carbon-heteroatom
2912:Grieco elimination
2698:Rieche formylation
2643:Passerini reaction
2573:Meerwein arylation
2493:Hydroxymethylation
2388:Favorskii reaction
2288:Chan rearrangement
2223:Biginelli reaction
2148:Aldol condensation
1994:2-Norbornyl cation
1969:Möbius aromaticity
1964:Markovnikov's rule
1859:Effective molarity
1804:BĂŒrgiâDunitz angle
1794:Bicycloaromaticity
1347:Eur. J. Org. Chem.
1225:10.1021/ed084p1979
799:
793:Ozone cracking in
574:
508:
459:
449:Reaction mechanism
429:N) gives a methyl
397:sodium bicarbonate
320:
306:
296:sodium borohydride
280:triphenylphosphine
124:Alkene Ozonolysis
92:carbonâcarbon bond
4939:
4938:
4935:
4934:
4931:
4930:
4923:WohlâAue reaction
4567:6+4 Cycloaddition
4384:Iodolactonization
3704:1,2-rearrangement
3669:WohlâAue reaction
3589:Sabatier reaction
3554:Pinnick oxidation
3519:Mozingo reduction
3464:Leuckart reaction
3419:Haloform reaction
3334:Criegee oxidation
3314:Collins oxidation
3264:Benkeser reaction
3259:Bechamp reduction
3229:Andrussow process
3214:Alcohol oxidation
3124:Edman degradation
3031:Haloform reaction
2980:
2979:
2967:Takai olefination
2932:Julia olefination
2758:Takai olefination
2633:Olefin metathesis
2508:Julia olefination
2433:Grignard reaction
2413:Fukuyama coupling
2328:Coupling reaction
2293:ChanâLam coupling
2163:Alkyne metathesis
2158:Alkane metathesis
2014:Phosphaethynolate
1919:George S. Hammond
1879:Electronic effect
1834:Conjugated system
1716:Stereospecificity
1711:Stereoselectivity
1676:Addition reaction
1665:organic reactions
1615:10.1021/cr040679f
1554:978-3-527-30673-2
1521:Collected Volumes
1502:Organic Syntheses
1470:10.1021/ja010166f
1464:(25): 6127â6141.
1458:J. Am. Chem. Soc.
1330:978-3-540-30030-4
1240:Organic Syntheses
1177:10.1021/ol061001k
1171:(15): 3199â3201.
1083:10.1021/cr040682z
1019:Collected Volumes
1012:Organic Syntheses
991:Collected Volumes
984:Organic Syntheses
964:978-0-471-72091-1
851:Norrish reactions
843:styrene-butadiene
695:dicarboxylic acid
514:isotopic labeling
331:functional groups
310:hydrogen peroxide
229:
228:
189:
188:
184:Cleavage products
61:organic chemistry
57:
56:
4969:
4918:Wenker synthesis
4908:Stollé synthesis
4763:Bobbitt reaction
4733:Auwers synthesis
4677:Povarov reaction
4602:Cyclopropanation
4540:
4539:
4534:Wenker synthesis
4289:Darzens reaction
4239:Bobbitt reaction
4084:Schmidt reaction
3889:Enyne metathesis
3664:Whiting reaction
3659:Wharton reaction
3604:Shapiro reaction
3594:Sarett oxidation
3559:Prévost reaction
3369:Emde degradation
3179:Wohl degradation
3159:Ruff degradation
3129:Emde degradation
3026:Grignard reagent
2962:Shapiro reaction
2947:McMurry reaction
2814:
2813:
2778:Ullmann reaction
2743:Stollé synthesis
2733:Stetter reaction
2723:Shapiro reaction
2713:Sakurai reaction
2608:Negishi coupling
2588:Minisci reaction
2583:Michael reaction
2568:McMurry reaction
2563:Mannich reaction
2443:Hammick reaction
2438:Grignard reagent
2378:Enyne metathesis
2363:Doebner reaction
2353:Darzens reaction
2198:Barbier reaction
2188:Auwers synthesis
2115:
2114:
2089:Woodward's rules
2054:Superaromaticity
2044:Spiroaromaticity
1944:Inductive effect
1939:Hyperconjugation
1914:Hammett equation
1854:Edwards equation
1706:Regioselectivity
1657:
1650:
1643:
1634:
1633:
1627:
1626:
1609:(7): 2943â2989.
1603:Chemical Reviews
1598:
1592:
1591:
1565:
1559:
1558:
1532:
1526:
1524:
1517:
1488:
1482:
1481:
1452:
1446:
1445:
1427:
1421:
1420:
1418:
1402:Helv. Chim. Acta
1392:
1386:
1385:
1369:
1363:
1362:
1353:(8): 1625â1627.
1341:
1335:
1334:
1308:
1302:
1301:
1290:
1284:
1283:
1262:
1256:
1255:
1235:
1229:
1228:
1195:
1189:
1188:
1155:
1149:
1148:
1128:
1122:
1121:
1101:
1095:
1094:
1077:(7): 2990â3001.
1071:Chemical Reviews
1066:
1055:
1054:
1030:
1024:
1022:
1015:
1002:
996:
994:
987:
979:"Diphenaldehyde"
974:
968:
967:
944:
927:biotechnological
922:Trametes hirsuta
813:was shown to be
777:
685:
599:) are produced.
598:
590:
579:Other substrates
562:carboxylic acids
415:acetic anhydride
405:dimethyl sulfide
383:
375:to an aldehyde:
358:pelargonic acids
292:dimethyl sulfide
254:potassium iodide
245:carboxylic acids
221:
206:
177:
145:
144:
121:
120:
101:
94:are replaced by
89:
69:organic reaction
49:
19:
18:
4977:
4976:
4972:
4971:
4970:
4968:
4967:
4966:
4942:
4941:
4940:
4927:
4828:Gewald reaction
4711:
4538:
4519:Skraup reaction
4354:Graham reaction
4349:Gewald reaction
4180:
4173:
3695:
3688:
3644:Swern oxidation
3629:Stahl oxidation
3574:Riley oxidation
3529:Omega oxidation
3489:Luche reduction
3439:Jones oxidation
3404:Glycol cleavage
3399:Ganem oxidation
3344:Davis oxidation
3339:Dakin oxidation
3274:Birch reduction
3224:Amide reduction
3190:
3183:
3144:Hooker reaction
3106:
3100:
2988:
2986:
2976:
2972:Wittig reaction
2860:
2856:Wittig reaction
2831:Hooker reaction
2812:
2793:Wittig reaction
2768:Thorpe reaction
2753:Suzuki reaction
2738:Stille reaction
2673:Quelet reaction
2548:Kumada coupling
2498:Ivanov reaction
2488:Hydrovinylation
2468:Hiyama coupling
2428:Glaser coupling
2238:Blaise reaction
2228:Bingel reaction
2213:Benary reaction
2130:
2128:
2122:
2113:
2009:Passive binding
1929:Homoaromaticity
1779:Baldwin's rules
1754:Antiaromaticity
1749:Anomeric effect
1725:
1667:
1661:
1631:
1630:
1599:
1595:
1588:
1566:
1562:
1555:
1533:
1529:
1519:
1489:
1485:
1453:
1449:
1442:
1428:
1424:
1393:
1389:
1370:
1366:
1342:
1338:
1331:
1309:
1305:
1292:
1291:
1287:
1274:(11): 745â752.
1263:
1259:
1236:
1232:
1196:
1192:
1156:
1152:
1139:(10): 807â810.
1129:
1125:
1118:
1102:
1098:
1067:
1058:
1051:
1031:
1027:
1017:
1003:
999:
989:
975:
971:
965:
945:
941:
936:
906:
898:
882:polychloroprene
823:
787:
775:
771:
767:
763:
759:
755:
751:
747:
743:
739:
735:
731:
727:
723:
719:
715:
714:
709:
683:
679:
675:
671:
667:
663:
659:
655:
651:
647:
643:
639:
635:
631:
627:
623:
605:
596:
588:
581:
542:
527:
451:
443:
439:
433:and an aldehyde
428:
420:
402:
373:terminal alkene
371:converting the
350:Dichloromethane
217:
202:
175:
168:
161:
156:
119:
99:
88:
84:
45:
17:
12:
11:
5:
4975:
4965:
4964:
4962:Cycloadditions
4959:
4954:
4937:
4936:
4933:
4932:
4929:
4928:
4926:
4925:
4920:
4915:
4910:
4905:
4900:
4895:
4890:
4885:
4880:
4875:
4870:
4865:
4860:
4855:
4850:
4845:
4840:
4835:
4833:Hantzsch ester
4830:
4825:
4820:
4815:
4810:
4805:
4800:
4795:
4790:
4785:
4780:
4775:
4770:
4765:
4760:
4755:
4750:
4745:
4743:Banert cascade
4740:
4735:
4730:
4725:
4719:
4717:
4713:
4712:
4710:
4709:
4704:
4699:
4694:
4689:
4684:
4682:Prato reaction
4679:
4674:
4669:
4664:
4659:
4654:
4649:
4644:
4639:
4634:
4629:
4624:
4619:
4614:
4609:
4604:
4599:
4594:
4589:
4584:
4579:
4574:
4569:
4564:
4559:
4554:
4548:
4546:
4537:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4486:
4481:
4476:
4471:
4466:
4461:
4456:
4451:
4446:
4441:
4436:
4431:
4426:
4421:
4416:
4411:
4406:
4401:
4396:
4391:
4386:
4381:
4376:
4371:
4366:
4361:
4356:
4351:
4346:
4341:
4336:
4331:
4326:
4321:
4316:
4311:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4271:
4266:
4261:
4256:
4251:
4246:
4241:
4236:
4231:
4226:
4221:
4216:
4211:
4206:
4201:
4196:
4191:
4185:
4183:
4175:
4174:
4172:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4136:
4131:
4126:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3971:
3966:
3961:
3956:
3951:
3946:
3941:
3936:
3931:
3926:
3921:
3916:
3911:
3906:
3901:
3896:
3891:
3886:
3881:
3876:
3871:
3866:
3861:
3856:
3851:
3846:
3841:
3836:
3831:
3826:
3821:
3816:
3811:
3806:
3801:
3796:
3791:
3786:
3781:
3776:
3774:Banert cascade
3771:
3766:
3761:
3756:
3751:
3746:
3741:
3736:
3731:
3726:
3721:
3716:
3711:
3706:
3700:
3698:
3694:Rearrangement
3690:
3689:
3687:
3686:
3684:Zinin reaction
3681:
3676:
3671:
3666:
3661:
3656:
3654:Wacker process
3651:
3646:
3641:
3636:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3436:
3431:
3429:Hydrogenolysis
3426:
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3386:
3381:
3379:Ătard reaction
3376:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3291:
3286:
3284:Bosch reaction
3281:
3276:
3271:
3266:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3216:
3211:
3206:
3201:
3195:
3193:
3189:Organic redox
3185:
3184:
3182:
3181:
3176:
3171:
3166:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3110:
3108:
3102:
3101:
3099:
3098:
3093:
3088:
3083:
3078:
3073:
3068:
3063:
3058:
3053:
3048:
3043:
3038:
3033:
3028:
3023:
3021:Esterification
3018:
3013:
3008:
3003:
2998:
2992:
2990:
2982:
2981:
2978:
2977:
2975:
2974:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2909:
2904:
2899:
2894:
2889:
2884:
2879:
2874:
2868:
2866:
2862:
2861:
2859:
2858:
2853:
2848:
2843:
2838:
2833:
2828:
2822:
2820:
2811:
2810:
2805:
2800:
2798:Wurtz reaction
2795:
2790:
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2720:
2715:
2710:
2705:
2700:
2695:
2690:
2685:
2680:
2675:
2670:
2668:Prins reaction
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:
2483:Hydrocyanation
2480:
2475:
2470:
2465:
2460:
2455:
2453:Henry reaction
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2315:
2310:
2305:
2300:
2295:
2290:
2285:
2280:
2275:
2270:
2265:
2260:
2255:
2250:
2245:
2240:
2235:
2230:
2225:
2220:
2215:
2210:
2205:
2200:
2195:
2190:
2185:
2180:
2175:
2170:
2165:
2160:
2155:
2153:Aldol reaction
2150:
2145:
2140:
2134:
2132:
2127:Carbon-carbon
2124:
2123:
2112:
2111:
2106:
2104:Zaitsev's rule
2101:
2096:
2091:
2086:
2081:
2076:
2071:
2066:
2061:
2056:
2051:
2049:Steric effects
2046:
2041:
2036:
2031:
2026:
2021:
2016:
2011:
2006:
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1966:
1961:
1956:
1951:
1946:
1941:
1936:
1931:
1926:
1921:
1916:
1911:
1906:
1901:
1896:
1891:
1886:
1881:
1876:
1871:
1866:
1861:
1856:
1851:
1846:
1841:
1836:
1831:
1826:
1821:
1816:
1811:
1806:
1801:
1796:
1791:
1786:
1781:
1776:
1771:
1766:
1761:
1756:
1751:
1746:
1741:
1736:
1730:
1727:
1726:
1724:
1723:
1718:
1713:
1708:
1703:
1701:Redox reaction
1698:
1693:
1688:
1686:Polymerization
1683:
1678:
1672:
1669:
1668:
1660:
1659:
1652:
1645:
1637:
1629:
1628:
1593:
1586:
1560:
1553:
1527:
1483:
1447:
1440:
1422:
1409:(4): 930â940.
1387:
1364:
1336:
1329:
1313:Name Reactions
1303:
1285:
1257:
1230:
1205:J. Chem. Educ.
1190:
1150:
1123:
1116:
1096:
1056:
1050:978-0632020171
1049:
1025:
997:
969:
963:
938:
937:
935:
932:
931:
930:
918:
912:
905:
902:
897:
894:
847:nitrile rubber
835:natural rubber
827:ozone cracking
822:
819:
811:natural rubber
795:natural rubber
786:
783:
779:
778:
773:
769:
765:
761:
757:
753:
749:
745:
741:
737:
733:
729:
725:
721:
717:
712:
711:
691:brassylic acid
687:
686:
681:
677:
673:
669:
665:
661:
657:
653:
649:
645:
641:
637:
633:
629:
625:
604:
601:
580:
577:
576:
575:
550:acid anhydride
544:Ozonolysis of
541:
538:
526:
523:
510:
509:
463:Rudolf Criegee
450:
447:
446:
445:
441:
437:
436:Using TsOH; Ac
434:
426:
418:
411:
400:
385:
384:
348:the reaction.
227:
226:
223:
222:
215:
208:
207:
200:
196:
195:
191:
190:
187:
186:
180:
179:
171:
170:
164:
163:
159:
152:
151:
141:
140:
136:
135:
130:
129:Reaction type
126:
125:
118:
115:
110:conditions.
86:
55:
54:
51:
50:
43:
39:
38:
34:
33:
28:
27:Reaction type
24:
23:
15:
9:
6:
4:
3:
2:
4974:
4963:
4960:
4958:
4955:
4953:
4950:
4949:
4947:
4924:
4921:
4919:
4916:
4914:
4911:
4909:
4906:
4904:
4901:
4899:
4896:
4894:
4891:
4889:
4886:
4884:
4881:
4879:
4876:
4874:
4871:
4869:
4866:
4864:
4861:
4859:
4856:
4854:
4851:
4849:
4846:
4844:
4843:Herz reaction
4841:
4839:
4836:
4834:
4831:
4829:
4826:
4824:
4821:
4819:
4816:
4814:
4811:
4809:
4806:
4804:
4801:
4799:
4796:
4794:
4791:
4789:
4786:
4784:
4781:
4779:
4776:
4774:
4771:
4769:
4766:
4764:
4761:
4759:
4756:
4754:
4751:
4749:
4746:
4744:
4741:
4739:
4736:
4734:
4731:
4729:
4726:
4724:
4721:
4720:
4718:
4714:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4660:
4658:
4655:
4653:
4650:
4648:
4645:
4643:
4640:
4638:
4635:
4633:
4630:
4628:
4625:
4623:
4620:
4618:
4615:
4613:
4610:
4608:
4605:
4603:
4600:
4598:
4595:
4593:
4590:
4588:
4585:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4549:
4547:
4545:
4544:Cycloaddition
4541:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4485:
4482:
4480:
4477:
4475:
4472:
4470:
4467:
4465:
4462:
4460:
4457:
4455:
4452:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4400:
4397:
4395:
4392:
4390:
4389:Isay reaction
4387:
4385:
4382:
4380:
4377:
4375:
4372:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:
4322:
4320:
4317:
4315:
4312:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4287:
4285:
4284:Cycloaddition
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4265:
4262:
4260:
4257:
4255:
4252:
4250:
4247:
4245:
4242:
4240:
4237:
4235:
4232:
4230:
4227:
4225:
4222:
4220:
4217:
4215:
4212:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4186:
4184:
4182:
4179:Ring forming
4176:
4170:
4167:
4165:
4162:
4160:
4157:
4155:
4152:
4150:
4147:
4145:
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4079:Rupe reaction
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3920:
3917:
3915:
3912:
3910:
3907:
3905:
3902:
3900:
3897:
3895:
3892:
3890:
3887:
3885:
3882:
3880:
3877:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3805:
3802:
3800:
3797:
3795:
3792:
3790:
3787:
3785:
3782:
3780:
3777:
3775:
3772:
3770:
3767:
3765:
3762:
3760:
3757:
3755:
3752:
3750:
3747:
3745:
3742:
3740:
3737:
3735:
3732:
3730:
3727:
3725:
3722:
3720:
3717:
3715:
3712:
3710:
3707:
3705:
3702:
3701:
3699:
3697:
3691:
3685:
3682:
3680:
3677:
3675:
3672:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3469:Ley oxidation
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3437:
3435:
3434:Hydroxylation
3432:
3430:
3427:
3425:
3424:Hydrogenation
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3359:DNA oxidation
3357:
3355:
3352:
3350:
3349:Deoxygenation
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3239:Aromatization
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3207:
3205:
3202:
3200:
3197:
3196:
3194:
3192:
3186:
3180:
3177:
3175:
3172:
3170:
3167:
3165:
3162:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3111:
3109:
3103:
3097:
3094:
3092:
3089:
3087:
3084:
3082:
3079:
3077:
3076:Reed reaction
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3057:
3054:
3052:
3049:
3047:
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3022:
3019:
3017:
3014:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2993:
2991:
2987:bond forming
2983:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2892:Cope reaction
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2869:
2867:
2863:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2837:
2834:
2832:
2829:
2827:
2824:
2823:
2821:
2819:
2815:
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:
2719:
2716:
2714:
2711:
2709:
2706:
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:
2603:Nef synthesis
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2578:Methylenation
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:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2448:Heck reaction
2446:
2444:
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:
2376:
2374:
2371:
2369:
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:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2236:
2234:
2231:
2229:
2226:
2224:
2221:
2219:
2216:
2214:
2211:
2209:
2206:
2204:
2201:
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:
2135:
2133:
2129:bond forming
2125:
2121:
2116:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2094:Y-aromaticity
2092:
2090:
2087:
2085:
2082:
2080:
2079:Walsh diagram
2077:
2075:
2072:
2070:
2067:
2065:
2064:Taft equation
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2040:
2037:
2035:
2034:ÎŁ-aromaticity
2032:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2000:
1997:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1965:
1962:
1960:
1959:Marcus theory
1957:
1955:
1952:
1950:
1947:
1945:
1942:
1940:
1937:
1935:
1934:HĂŒckel's rule
1932:
1930:
1927:
1925:
1922:
1920:
1917:
1915:
1912:
1910:
1907:
1905:
1902:
1900:
1897:
1895:
1892:
1890:
1889:Evelyn effect
1887:
1885:
1882:
1880:
1877:
1875:
1872:
1870:
1869:Electron-rich
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1847:
1845:
1842:
1840:
1837:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1817:
1815:
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1784:Bema Hapothle
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1765:
1762:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1732:
1731:
1728:
1722:
1719:
1717:
1714:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1677:
1674:
1673:
1670:
1666:
1658:
1653:
1651:
1646:
1644:
1639:
1638:
1635:
1624:
1620:
1616:
1612:
1608:
1604:
1597:
1589:
1583:
1579:
1575:
1571:
1564:
1556:
1550:
1546:
1542:
1538:
1531:
1522:
1516:
1512:
1508:
1504:
1503:
1498:
1496:
1487:
1479:
1475:
1471:
1467:
1463:
1460:
1459:
1451:
1443:
1441:0-12-073102-9
1437:
1433:
1426:
1417:
1412:
1408:
1404:
1403:
1398:
1391:
1383:
1380:(in German).
1379:
1375:
1368:
1360:
1356:
1352:
1349:
1348:
1340:
1332:
1326:
1322:
1318:
1314:
1307:
1299:
1295:
1289:
1281:
1277:
1273:
1270:
1269:
1261:
1253:
1249:
1245:
1241:
1234:
1226:
1222:
1218:
1214:
1210:
1207:
1206:
1201:
1194:
1186:
1182:
1178:
1174:
1170:
1167:
1166:
1161:
1154:
1146:
1142:
1138:
1134:
1127:
1119:
1113:
1109:
1108:
1100:
1092:
1088:
1084:
1080:
1076:
1072:
1065:
1063:
1061:
1052:
1046:
1042:
1038:
1037:
1029:
1020:
1014:
1013:
1008:
1001:
992:
986:
985:
980:
973:
966:
960:
956:
955:
950:
943:
939:
928:
924:
923:
919:
916:
913:
911:
908:
907:
901:
893:
891:
887:
883:
879:
875:
871:
867:
863:
858:
856:
852:
848:
844:
840:
839:polybutadiene
836:
832:
828:
818:
816:
812:
808:
804:
796:
791:
782:
708:
707:
706:
704:
700:
696:
692:
622:
621:
620:
618:
617:nonanoic acid
614:
610:
600:
594:
586:
585:azo compounds
571:
567:
566:
565:
563:
559:
555:
551:
547:
537:
535:
531:
522:
519:
515:
504:
500:
499:
498:
496:
492:
488:
484:
480:
476:
472:
468:
464:
455:
435:
432:
424:
423:triethylamine
416:
412:
410:
406:
398:
394:
390:
389:
388:
382:
378:
377:
376:
374:
370:
365:
363:
359:
355:
351:
347:
343:
339:
336:
332:
328:
326:
317:
313:
311:
303:
299:
297:
293:
289:
285:
281:
276:
274:
271:
266:
263:
262:Sudan Red III
259:
255:
250:
246:
242:
238:
234:
224:
220:
216:
213:
210:
209:
205:
201:
198:
197:
192:
185:
181:
178:
172:
165:
162:
153:
150:
146:
142:
137:
134:
131:
128:
127:
122:
114:
111:
109:
105:
97:
93:
82:
78:
74:
70:
66:
62:
52:
48:
44:
41:
40:
35:
32:
29:
26:
25:
20:
4666:
3884:Ene reaction
3543:
3244:Autoxidation
3105:Degradation
2996:Azo coupling
2773:Ugi reaction
2373:Ene reaction
2173:Alkynylation
2024:Polyfluorene
2019:Polar effect
1884:Electrophile
1799:Bredt's rule
1769:Baird's rule
1739:Alpha effect
1606:
1602:
1596:
1569:
1563:
1536:
1530:
1520:
1506:
1500:
1494:
1486:
1461:
1456:
1450:
1431:
1425:
1406:
1400:
1390:
1381:
1377:
1367:
1350:
1345:
1339:
1312:
1306:
1297:
1288:
1271:
1266:
1260:
1243:
1239:
1233:
1211:(12): 1979.
1208:
1203:
1193:
1168:
1163:
1159:
1153:
1136:
1132:
1126:
1106:
1099:
1074:
1070:
1035:
1028:
1018:
1010:
1000:
990:
982:
972:
953:
949:March, Jerry
942:
920:
899:
878:antiozonants
859:
855:antiozonants
824:
800:
780:
688:
613:azelaic acid
606:
603:Applications
593:Nitrosamines
582:
543:
528:
518:benzaldehyde
511:
494:
482:
460:
386:
366:
354:Azelaic acid
324:
321:
307:
277:
267:
230:
219:RXNO:0000344
214:ontology ID
194:Identifiers
183:
174:
157:
148:
112:
90:). Multiple
64:
58:
37:Identifiers
2383:Ethenolysis
2029:Ring strain
1999:Nucleophile
1824:Clar's rule
1764:Aromaticity
807:repeat unit
803:polyolefins
477:or Criegee
308:The use of
278:The use of
73:unsaturated
22:Ozonolysis
4946:Categories
4667:Ozonolysis
4194:Annulation
3544:Ozonolysis
1663:Topics in
1587:3527306730
1165:Org. Lett.
1117:0123705517
934:References
833:, such as
831:elastomers
821:Occurrence
703:polyesters
699:polyamides
609:oleic acid
491:trioxolane
479:zwitterion
467:molozonide
362:oleic acid
333:, such as
75:bonds are
71:where the
65:ozonolysis
4181:reactions
3696:reactions
3191:reactions
3107:reactions
2989:reactions
2131:reactions
1133:Synthesis
290:dust, or
270:Reductive
237:aldehydes
139:Reaction
2074:Vinylogy
1744:Annulene
1691:Reagents
1623:16836305
1478:11414847
1185:16836365
1091:16836306
951:(2007),
904:See also
815:isoprene
760:H + HO
740:+ 0.5 O
724:CH=CH(CH
693:, a C13-
648:H} + 4 O
636:CH=CH(CH
554:diketone
342:pyridine
284:thiourea
249:methanol
233:alcohols
106:and the
104:oxidized
96:carbonyl
1734:A value
1509:: 183.
1246:: 150.
1213:Bibcode
874:blowout
866:tension
736:H + O
668:H} + CH
558:alkenes
546:alkynes
525:History
487:ozonide
369:eugenol
327:-oxides
273:work-up
241:ketones
108:work-up
77:cleaved
1621:
1584:
1551:
1476:
1438:
1384:: 7â9.
1327:
1183:
1114:
1089:
1047:
961:
896:Safety
845:, and
797:tubing
744:â CH
413:Using
409:acetal
399:(NaHCO
391:Using
346:buffer
338:ethers
335:benzyl
322:Amine
258:iodine
149:Alkene
67:is an
1041:55â57
890:Viton
870:tires
652:â HO
597:NâN=O
469:in a
440:O, Et
431:ester
243:, or
81:ozone
79:with
1619:PMID
1582:ISBN
1549:ISBN
1474:PMID
1436:ISBN
1351:1998
1325:ISBN
1181:PMID
1137:1980
1112:ISBN
1087:PMID
1045:ISBN
959:ISBN
925:, a
886:EPDM
764:C(CH
701:and
656:C(CH
421:O),
393:TsOH
356:and
288:zinc
1611:doi
1607:106
1574:doi
1541:doi
1511:doi
1466:doi
1462:123
1411:doi
1355:doi
1317:doi
1276:doi
1248:doi
1221:doi
1173:doi
1141:doi
1079:doi
1075:106
888:or
817:.
809:in
748:(CH
716:(CH
672:(CH
628:(CH
589:N=N
552:or
497:).
425:(Et
417:(Ac
403:);
239:or
212:RSC
100:C=O
59:In
4948::
1617:.
1605:.
1580:.
1572:.
1547:.
1539:.
1518:;
1507:65
1505:.
1499:.
1472:.
1407:86
1405:.
1399:.
1376:.
1323:.
1296:.
1272:14
1244:64
1242:.
1219:.
1209:84
1202:.
1179:.
1135:.
1085:.
1073:.
1059:^
1043:.
1016:;
1009:.
988:;
981:.
892:.
884:,
857:.
841:,
837:,
772:CO
770:11
756:CO
732:CO
730:11
710:CH
680:CO
664:CO
644:CO
624:CH
619::
564:.
395:;
286:,
282:,
235:,
63:,
1656:e
1649:t
1642:v
1625:.
1613::
1590:.
1576::
1557:.
1543::
1525:.
1513::
1495:S
1480:.
1468::
1444:.
1419:.
1413::
1382:7
1361:.
1357::
1333:.
1319::
1300:.
1282:.
1278::
1254:.
1250::
1227:.
1223::
1215::
1187:.
1175::
1169:8
1160:N
1147:.
1143::
1120:.
1093:.
1081::
1053:.
1023:.
995:.
776:H
774:2
768:)
766:2
762:2
758:2
754:7
752:)
750:2
746:3
742:2
738:3
734:2
728:)
726:2
722:7
720:)
718:2
713:3
684:H
682:2
678:7
676:)
674:2
670:3
666:2
662:7
660:)
658:2
654:2
650:3
646:2
642:7
640:)
638:2
634:7
632:)
630:2
626:3
595:(
587:(
495:4
493:(
483:3
442:3
438:2
427:3
419:2
401:3
325:N
176:â
167:+
160:3
158:O
155:+
98:(
87:3
85:O
83:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.