303:
262:
331:
351:
477:
402:
806:
449:
198:
607:
783:
666:
739:, that is, for an application in organic synthesis. Considering the environmental concerns for most of the chemical catalysts, the use of enzymes is considered a greener alternative. BVMOs in particular are interesting for application because they fulfil a range of criteria typically sought for in biocatalysis: besides their ability to catalyse a synthetically useful reaction, some natural
326:
of the
Criegee intermediate). Keeping this structure in mind, it makes sense that the substituent that can maintain positive charge the best would be most likely to migrate. The higher the degree of substitution, the more stable a carbocation generally is. Therefore, the tertiary > secondary >
346:
between the peroxyacid and the non-migrating substituent. If the bulkier group is placed antiperiplanar to the peroxide group, the gauche interaction between the substituent on the forming ester and the carbonyl group of the peroxyacid will be reduced. Thus, it is the bulkier group that will prefer
774:
Zoapatanol is a biologically active molecule that occurs naturally in the zeopatle plant, which has been used in Mexico to make a tea that can induce menstruation and labor. In 1981, Vinayak Kane and Donald Doyle reported a synthesis of zoapatanol. They used the Baeyer–Villiger oxidation to make a
2262:
Levine, Seymour D.; Adams, Richard E.; Chen, Robert; Cotter, Mary Lou; Hirsch, Allen F.; Kane, Vinayak V.; Kanojia, Ramesh M.; Shaw, Charles; Wachter, Michael P.; Chin, Eva; Huettemann, Richard; Ostrowski, Paul (1979). "Zoapatanol and
Montanol, Novel Oxepane Diterpenoids, from the Mexican Plant
628:
would be advantageous, making the reaction more environmentally friendly as the sole byproduct is water. Benzeneseleninic acid derivatives as catalysts have been reported to give high selectivity with hydrogen peroxide as the oxidant. Another class of catalysts which show high selectivity with
468:. The three different mechanisms would each lead to a different distribution of labelled products. The Criegee intermediate would lead to a product only labelled on the carbonyl oxygen. The product of the Wittig and Pieper intermediate is only labeled on the
318:
on the substituent decrease the rate of migration. There are two explanations for this trend in migration ability. One explanation relies on the buildup of positive charge in the transition state for breakdown of the
Criegee intermediate (illustrated by the
629:
hydrogen peroxide as the oxidant are solid Lewis acid catalysts such as stannosilicates. Among stannosilicates, particularly the zeotype Sn-beta and the amorphous Sn-MCM-41 show promising activity and close to full selectivity towards the desired product.
472:
of the ester. The Baeyer and
Villiger intermediate leads to a 1:1 distribution of both of the above products. The outcome of the labelling experiment supported the Criegee intermediate, which is now the generally accepted pathway.
2015:
Fiorentini, Filippo; Geier, Martina; Binda, Claudia; Winkler, Margit; Faber, Kurt; Hall, Mélanie; Mattevi, Andrea (15 April 2016). "Biocatalytic
Characterization of Human FMO5: Unearthing Baeyer–Villiger Reactions in Humans".
756:
and/or reactivity. Another advantage of using enzymes for the reaction is their frequently observed regio- and enantioselectivity, owed to the steric control of substrate orientation during catalysis within the enzyme's
1727:
Renz, M; Blasco, T; Corma, A; Fornés, V; Jensen, R; Nemeth, L (18 October 2002). "Selective and shape-selective Baeyer-Villiger oxidations of aromatic aldehydes and cyclic ketones with Sn-beta zeolites and H2O2".
743:
were found to have a very large substrate scope (i.e. their reactivity was not restricted to a single compound, as often assumed in enzyme catalysis), they can be easily produced on a large scale, and because the
1660:
Ferrini, Paola; Dijkmans, Jan; Clercq, Rik De; Vyver, Stijn Van de; Dusselier, Michiel; Jacobs, Pierre A.; Sels, Bert F. (2017). "Lewis acid catalysis on single site Sn centers incorporated into silica hosts".
1462:
Cavarzan, Alessandra; Scarso, Alessandro; Sgarbossa, Paolo; Michelin, Rino A.; Strukul, Giorgio (2010). "Green
Catalytic Baeyer–Villiger Oxidation with Hydrogen Peroxide in Water Mediated by Pt(II) Catalysts".
1624:
ten Brink, Gerd-Jan; Vis, Jan-Martijn; Arends, Isabel W. C. E.; Sheldon, Roger A. (2001). "Selenium-Catalyzed
Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer−Villiger Reactions in Homogeneous Solution".
293:
group to be antiperiplanar to the migrating group. This allows for optimum overlap of the oxygen nonbonding orbital with the 𝛔* orbital of the migrating group. This migration step is also (at least
5592:
599:. However, methods have been developed that will allow for the tolerance of these functional groups. In 1962, G. B. Payne reported that the use of hydrogen peroxide in the presence of a
1823:
Sheng, Dawei; Ballou, David P.; Massey, Vincent (1 September 2001). "Mechanistic
Studies of Cyclohexanone Monooxygenase: Chemical Properties of Intermediates Involved in Catalysis".
966:
Crudden, Cathleen M.; Chen, Austin C.; Calhoun, Larry A. (2000). "A Demonstration of the
Primary Stereoelectronic Effect in the Baeyer-Villiger Oxidation of α-Fluorocyclohexanones".
705:, and theoretical studies suggest that the reaction proceeds through the same Criegee intermediate as observed in the chemical reaction. After the rearrangement step forming the
261:
1866:
Polyak, Iakov; Reetz, Manfred T.; Thiel, Walter (8 February 2012). "Quantum
Mechanical/Molecular Mechanical Study on the Mechanism of the Enzymatic Baeyer–Villiger Reaction".
222:. This makes the carbonyl group more susceptible to be attacked by the peroxyacid. Next, the peroxyacid attacks the carbon of the carbonyl group forming what is known as the
4708:
4653:
330:
5421:
4763:
1688:
Corma, A; Navarro, MT; Nemeth, L; Renz, M (7 November 2001). "Sn-MCM-41—a heterogeneous selective catalyst for the Baeyer-Villiger oxidation with hydrogen peroxide".
4913:
3547:
358:
The migrating group in acyclic ketones, usually, is not 1° alkyl group. However, they may be persuaded to migrate in preference to the 2° or 3° groups by using CF
5642:
1127:
Hawthorne, M. Frederick; Emmons, William D.; McCallum, K. S. (1958). "A Re-examination of the Peroxyacid Cleavage of Ketones. I. Relative Migratory Aptitudes".
5416:
4518:
1498:
Schweitzer-Chaput, Bertrand; Kurtén, Theo; Klussmann, Martin (2015). "Acid-Mediated Formation of Radicals or Baeyer-Villiger Oxidation from Criegee Adducts".
413:
of the Baeyer–Villiger oxidation that seemed to fit with observed reaction outcomes. These three reaction mechanisms can really be split into two pathways of
3242:
302:
4288:
2439:
5088:
3032:
338:
Another explanation uses stereoelectronic effects and steric arguments. As mentioned, the substituent that is antiperiplanar to the peroxide group in the
5183:
3287:
5163:
4658:
3825:
677:
called Baeyer-Villiger monooxygenases (BVMOs) perform the oxidation analogously to the chemical reaction. To facilitate this chemistry, BVMOs contain a
3706:
3262:
386:
In 1899, Adolf Baeyer and Victor Villiger first published a demonstration of the reaction that we now know as the Baeyer–Villiger oxidation. They used
5253:
350:
273:. The primary stereoelectronic effect in the Baeyer–Villiger oxidation refers to the necessity of the oxygen-oxygen bond in the peroxide group to be
5008:
732:. Human FMO5 was in fact shown to be able to catalyse Baeyer-Villiger reactions, indicating that the reaction may occur in the human body as well.
2475:
2205:
Li, Guangyue; Garcia-Borràs, Marc; Fürst, Maximilian J. L. J.; Ilie, Adriana; Fraaije, Marco W.; Houk, K. N.; Reetz, Manfred T. (22 August 2018).
3840:
5486:
4943:
5436:
5048:
5028:
4988:
3795:
1597:
Payne, G. B. (1962). "A Simplified Procedure for Epoxidation by Benzonitrile-Hydrogen Peroxide. Selective Oxidation of 2-Allylcyclohexanone".
5582:
5507:
5391:
4003:
3407:
2738:
1554:
1222:
1171:
873:
5577:
5406:
5063:
4918:
4548:
1347:
Doering, W. von E.; Dorfman, Edwin (1953). "Mechanism of the Peracid Ketone-Ester Conversion. Analysis of Organic Compounds for Oxygen-18".
141:
5741:
4393:
3630:
4753:
4243:
3918:
1322:
5657:
5441:
4463:
802:
to anticancer agent testololactone by use of a Baeyer–Villiger oxidation induced by fungus that produces Baeyer-Villiger monooxygenases.
5018:
5652:
5366:
5228:
4983:
943:
5542:
5013:
4928:
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4743:
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2763:
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1991:
5647:
5607:
5557:
5033:
4783:
4713:
3202:
1435:
Gallagher, T. F.; Kritchevsky, Theodore H. (1950). "Perbenzoic Acid Oxidation of 20-Ketosteroids and the Stereochemistry of C-17".
979:
5243:
4848:
3741:
3462:
2297:
Kane, Vinayak V.; Doyle, Donald L. (1981). "Total Synthesis of (±) Zoapatanol: A Stereospecific Synthesis of a Key Intermediate".
1741:
5736:
5233:
2773:
5401:
5158:
5108:
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3721:
3297:
3052:
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4308:
2432:
2095:
Fürst, Maximilian J. L. J.; Romero, Elvira; Gómez Castellanos, J. Rúben; Fraaije, Marco W.; Mattevi, Andrea (7 December 2018).
717:
5687:
5471:
5411:
4813:
4788:
4698:
4278:
4158:
3192:
2688:
1544:
559:. In addition, using organic peroxides and hydrogen peroxide tends to generate more side-reactivity due to their promiscuity.
5572:
5058:
4853:
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197:
5677:
5263:
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4228:
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3337:
3187:
669:
Reaction mechanism of the flavin cofactor to catalyse the Baeyer-Villiger reaction in Baeyer-Villiger monooxygenase enzymes.
5637:
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510:
282:
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460:
and Edwin Dorfman elucidated the correct pathway for the reaction mechanism of the Baeyer–Villiger oxidation by using
5597:
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5103:
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4078:
4018:
3610:
3317:
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3152:
476:
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134:
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4148:
3447:
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2904:
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1546:
Comprehensive Organic Synthesis – Selectivity, Strategy and Efficiency in Modern Organic Chemistry, Volumes 1 – 9
610:
Payne reported that different reagents will give different outcomes when there are more than one functional group
5662:
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5238:
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3572:
3532:
3307:
3177:
2693:
2683:
2613:
805:
638:
552:
269:
The products of the Baeyer–Villiger oxidation are believed to be controlled through both primary and secondary
5128:
4108:
3132:
2678:
2558:
5341:
2062:
Fürst, Maximilian J. L. J.; Gran-Scheuch, Alejandro; Aalbers, Friso S.; Fraaije, Marco W. (6 December 2019).
809:Świzdor reported that a Baeyer-Villiger monooxygenase could change dehydroepiandrosterone into testololactone
5751:
5632:
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5188:
4908:
4858:
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2603:
1195:
682:
603:
catalyst will produce the epoxide from alkenyl ketones, while use of peroxyacetic acid will form the ester.
535:
in the case of the peroxides). Therefore, the reactivity trend shows TFPAA > 4-nitroperbenzoic acid >
517:
448:
387:
270:
2207:"Overriding Traditional Electronic Effects in Biocatalytic Baeyer–Villiger Reactions by Directed Evolution"
5371:
5093:
4843:
4823:
4798:
4748:
4663:
4638:
4593:
4563:
4543:
4513:
4478:
4433:
4408:
4383:
4268:
4193:
3973:
3666:
3602:
3402:
3127:
3047:
2733:
2708:
2485:
2480:
1967:
799:
555:. The peroxides are much less reactive than the peroxyacids. The use of hydrogen peroxide even requires a
521:
57:
5707:
4453:
3077:
1009:
299:) assisted by two or three peroxyacid units enabling the hydroxyl proton to shuttle to its new position.
5293:
5248:
4963:
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4903:
4838:
4818:
4733:
4728:
4693:
4648:
4633:
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3726:
3302:
3257:
3087:
2823:
2543:
2505:
1968:"Molecular Mechanism of Phase I and Phase II Drug-Metabolizing Enzymes: Implications for Detoxification"
745:
505:
Although many different peroxyacids are used for the Baeyer–Villiger oxidation, some of the more common
422:
323:
243:
2753:
2748:
5346:
1935:
1910:
5476:
5426:
5376:
5356:
5203:
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3512:
3472:
3432:
3397:
3327:
3082:
2952:
2927:
2465:
1072:; Sheldon, R. A. (2004). "The Baeyer-Villiger Reaction: New Developments toward Greener Procedures".
710:
698:
442:
223:
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3492:
3437:
3207:
3057:
3002:
2873:
2788:
2648:
2573:
1381:
Doering, W. von E.; Speers, Louise (1950). "The Peracetic Acid Cleavage of Unsymmetrical Ketones".
749:
702:
532:
343:
227:
2718:
865:
314:
groups are more apt to migrate than primary alkyl groups but less so than secondary alkyl groups.
5431:
5381:
5351:
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4793:
4678:
4613:
4603:
4368:
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3172:
3072:
3007:
2932:
2778:
2643:
2578:
1480:
740:
410:
211:
2563:
2148:"Stabilization of cyclohexanone monooxygenase by computational and experimental library design"
1163:
441:. In this pathway, the peracid attacks the carbonyl carbon, producing what is now known as the
5168:
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4373:
4338:
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4248:
4203:
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4118:
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1515:
1289:
1218:
1167:
1089:
1043:
983:
939:
911:
869:
720:(FMOs), enzymes that also occur in the human body, functioning within the frontline metabolic
606:
595:. For instance, alkenes in the substrate, particularly when electron-rich, may be oxidized to
580:
548:
5702:
5547:
5517:
5461:
5386:
5318:
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5023:
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2118:
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1930:
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1281:
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1155:
1136:
1081:
1035:
975:
903:
857:
779:
that served as a crucial building block that ultimately led to the synthesis of zoapatanol.
642:
339:
285:
of the peroxide group. The secondary stereoelectronic effect refers to the necessity of the
187:
159:
43:
5612:
5303:
5138:
5133:
4428:
4413:
4358:
4313:
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4223:
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4128:
4123:
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3212:
3022:
3012:
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2793:
2713:
2538:
2533:
753:
729:
721:
686:
490:
239:
191:
47:
2583:
2553:
2146:
Fürst, Maximilian J. L. J.; Boonstra, Marjon; Bandstra, Selle; Fraaije, Marco W. (2019).
858:
17:
782:
665:
5617:
5527:
5466:
4558:
4468:
4438:
4213:
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3805:
3582:
3452:
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3237:
2937:
2833:
2608:
2470:
2386:
2355:
2239:
2206:
2182:
2147:
2123:
2097:"Side-Chain Pruning Has Limited Impact on Substrate Preference in a Promiscuous Enzyme"
2096:
819:
649:
ketone used dioxygen as the oxidant with a copper catalyst. Other catalysts, including
544:
540:
438:
418:
274:
235:
219:
2340:
2310:
1983:
1610:
5730:
5627:
5328:
5173:
5068:
4863:
4253:
4218:
4208:
4143:
4133:
4023:
3860:
3676:
3387:
3362:
3232:
2878:
2863:
2848:
2743:
2673:
2653:
2568:
1156:
1069:
247:
1484:
1026:
Yamabe, Shinichi (2007). "The Role of Hydrogen Bonds in Baeyer−Villiger Reactions".
4668:
4028:
3780:
3557:
3157:
2957:
2808:
2803:
2668:
2523:
1309:
Renz, Michael; Meunier, Bernard (1999). "100 Years of Baeyer-Villiger Oxidations".
736:
646:
645:
Baeyer–Villiger oxidations. The first reported instance of one such oxidation of a
469:
465:
430:
251:
1926:
1408:
Turner, Richard B. (1950). "Stereochemistry of the Peracid Oxidation of Ketones".
347:
to be antiperiplanar to the peroxide group, enhancing its aptitude for migration.
1272:
Hassall, C. H. (1957). "The Baeyer-Villiger Oxidation of Aldehydes and Ketones".
894:
Krow, Grant R. (1993). "The Baeyer-Villiger Oxidation of Ketones and Aldehydes".
3167:
2813:
2783:
2548:
2327:
Kane, Vinayak V.; Doyle, Donald L. (1981). "Total Synthesis of (±) Zoapatanol".
1285:
907:
758:
568:
320:
310:
The migratory ability is ranked tertiary > secondary > aryl > primary.
277:
to the group that migrates. This orientation facilitates optimum overlap of the
175:
82:
2376:
2029:
5451:
4978:
4328:
2417:
1674:
1255:
414:
278:
215:
2230:
2173:
2113:
2080:
2063:
2037:
1944:
1887:
1844:
1801:
1749:
1705:
1323:
10.1002/(SICI)1099-0690(199904)1999:4<737::AID-EJOC737>3.0.CO;2-B
480:
The different possible outcomes of Dorfman and Doering's labelling experiment
654:
576:
572:
461:
426:
295:
286:
179:
2395:
2248:
2191:
2132:
2045:
2001:
1952:
1895:
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1809:
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1511:
1476:
1093:
1047:
987:
980:
10.1002/1521-3773(20000818)39:16<2851::aid-anie2851>3.0.co;2-y
2858:
2528:
2222:
1742:
10.1002/1521-3765(20021018)8:20<4708::AID-CHEM4708>3.0.CO;2-U
650:
600:
592:
556:
506:
434:
395:
290:
2280:
1911:"Flavoprotein monooxygenases, a diverse class of oxidative biocatalysts"
1909:
van Berkel, W. J. H.; Kamerbeek, N. M.; Fraaije, M. W. (5 August 2006).
1448:
1421:
1394:
1360:
1140:
786:
Kane and Doyle used a Baeyer-Villiger oxidation to synthesize zoapatanol
575:
when performing the Baeyer–Villiger oxidation can cause the undesirable
2518:
796:
776:
697:
first reduces the cofactor, which allows it subsequently to react with
625:
596:
584:
391:
311:
183:
171:
2164:
1879:
1836:
1793:
1638:
1085:
1039:
1697:
701:. The resulting peroxyflavin is the catalytic entity oxygenating the
674:
588:
231:
167:
1239:
713:
water to form oxidized flavin, thereby closing the catalytic cycle.
864:. Burlington; San Diego; London: Elsevier Academic Press. p.
804:
781:
725:
706:
694:
690:
664:
605:
536:
531:(i.e.: stronger acidity) of the corresponding carboxylic acid (or
475:
447:
400:
255:
163:
90:
1776:
Leisch, Hannes; Morley, Krista; Lau, Peter C. K. (13 July 2011).
2064:"Baeyer–Villiger Monooxygenases: Tunable Oxidative Biocatalysts"
1778:"Baeyer−Villiger Monooxygenases: More Than Just Green Chemistry"
2902:
2421:
860:
Strategic Applications of Named Reactions in Organic Synthesis
1162:(4th ed.). Canada: W. W. Norton & Company. p.
437:
with no dioxirane formation. Carbon attack was suggested by
349:
329:
301:
260:
196:
936:
Advanced Organic Chemistry: Part B: Reactions and Synthesis
795:
In 2013, Alina Świzdor reported the transformation of the
735:
BVMOs have been widely studied due to their potential as
709:
product, a hydroxyflavin remains, which spontaneously
5593:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
265:
Reaction mechanism of the Baeyer-Villiger oxidation.
5500:
5327:
4962:
4477:
3972:
3889:
3769:
3649:
3601:
2911:
2356:"Baeyer-Villiger Oxidation of Some C19 Steroids by
752:could be applied to produce variants with improved
417:attack – on either the oxygen or the carbon of the
1109:Name Reactions of Functional Group Transformations
938:(5th ed.). New York: Springer. p. 1135.
405:Original reactions reported by Baeyer and Villiger
4654:Divinylcyclopropane-cycloheptadiene rearrangement
1577:"Page 1 The Asymmetric Baeyer-Villiger Oxidation"
1154:Jones, Jr., Maitland; Fleming, Steven A. (2010).
242:leaves. This migration step is thought to be the
934:Carey, Francis A.; Sundberg, Richard J. (2007).
452:Proposed Baeyer-Villiger oxidation intermediates
334:Resonance structures of the Criegee intermediate
4914:Thermal rearrangement of aromatic hydrocarbons
3548:Thermal rearrangement of aromatic hydrocarbons
1543:(1991). Trost, Barry M.; Fleming, Ian (eds.).
1240:"Einwirkung des Caro'schen Reagens auf Ketone"
421:. Attack on oxygen could lead to two possible
5643:Lectka enantioselective beta-lactam synthesis
2433:
8:
5422:Inverse electron-demand Diels–Alder reaction
3243:Heterogeneous metal catalyzed cross-coupling
1342:
1340:
1338:
1336:
1334:
1332:
4764:Lobry de Bruyn–Van Ekenstein transformation
1570:
1568:
1566:
5324:
3598:
2899:
2440:
2426:
2418:
2413:Animation of the Baeyer–Villiger oxidation
1936:11370/99a1ac5c-d4a4-4612-90a3-4fe1d4d03a11
1267:
1265:
1122:
1120:
1118:
929:
927:
520:(TFPAA). The general trend is that higher
342:will migrate. This transition state has a
31:
5254:Petrenko-Kritschenko piperidone synthesis
4709:Fritsch–Buttenberg–Wiechell rearrangement
2385:
2375:
2238:
2181:
2163:
2122:
2112:
2079:
1934:
1771:
1769:
1767:
1376:
1374:
1372:
1370:
1107:Li, Jie Jack; Corey, E. J., eds. (2007).
1063:
1061:
1059:
1057:
493:of the group that transfers, i.e.: it is
194:who first reported the reaction in 1899.
5417:Intramolecular Diels–Alder cycloaddition
2211:Journal of the American Chemical Society
2057:
2055:
1868:Journal of the American Chemical Society
1535:
1533:
1531:
1529:
1383:Journal of the American Chemical Society
1238:Baeyer, Adolf; Villiger, Victor (1899).
1189:
1187:
1185:
1183:
961:
959:
957:
955:
689:(see figure on the right), the cellular
390:to make the corresponding lactones from
68:
2322:
2320:
1500:Angewandte Chemie International Edition
1003:
1001:
999:
997:
851:
849:
847:
845:
843:
841:
839:
837:
835:
831:
5437:Metal-centered cycloaddition reactions
5089:Debus–Radziszewski imidazole synthesis
3033:Bodroux–Chichibabin aldehyde synthesis
2292:
2290:
1215:Reactions, Rearrangements and Reagents
889:
887:
885:
856:Kürti, László; Czakó, Barbara (2005).
5583:Diazoalkane 1,3-dipolar cycloaddition
5487:Vinylcyclopropane (5+2) cycloaddition
5392:Diazoalkane 1,3-dipolar cycloaddition
5164:Hurd–Mori 1,2,3-thiadiazole synthesis
4659:Dowd–Beckwith ring-expansion reaction
3826:Hurd–Mori 1,2,3-thiadiazole synthesis
2739:LFER solvent coefficients (data page)
7:
4394:Sharpless asymmetric dihydroxylation
3631:Methoxymethylenetriphenylphosphorane
633:Asymmetric Baeyer-Villiger oxidation
591:are a few of the groups that can be
234:group migrates to the oxygen of the
4519:Allen–Millar–Trippett rearrangement
1966:Iyanagi, Takashi (1 January 2007).
1010:"Chemistry 115 Handouts: Oxidation"
748:of many BVMOs has been determined,
624:The use of hydrogen peroxide as an
620:Catalytic Baeyer-Villiger oxidation
5658:Nitrone-olefin (3+2) cycloaddition
5653:Niementowski quinazoline synthesis
5442:Nitrone-olefin (3+2) cycloaddition
5367:Azide-alkyne Huisgen cycloaddition
5229:Niementowski quinazoline synthesis
4984:Azide-alkyne Huisgen cycloaddition
4289:Meerwein–Ponndorf–Verley reduction
3841:Leimgruber–Batcho indole synthesis
1111:. Hoboken, NJ: Wiley-Interscience.
489:The migration does not change the
425:: Baeyer and Villiger suggested a
25:
5482:Trimethylenemethane cycloaddition
5184:Johnson–Corey–Chaykovsky reaction
5049:Cadogan–Sundberg indole synthesis
5029:Bohlmann–Rahtz pyridine synthesis
4989:Baeyer–Emmerling indole synthesis
3796:Cadogan–Sundberg indole synthesis
3288:Johnson–Corey–Chaykovsky reaction
716:BVMOs are closely related to the
354:Steric bulk influencing migration
230:, one of the substituents on the
5578:Cook–Heilbron thiazole synthesis
5407:Hexadehydro Diels–Alder reaction
5234:Niementowski quinoline synthesis
5064:Cook–Heilbron thiazole synthesis
5009:Bischler–Möhlau indole synthesis
4919:Tiffeneau–Demjanov rearrangement
4549:Baker–Venkataraman rearrangement
3707:Horner–Wadsworth–Emmons reaction
3378:Mizoroki-Heck vs. Reductive Heck
3263:Horner–Wadsworth–Emmons reaction
2774:Neighbouring group participation
2152:Biotechnology and Bioengineering
1972:International Review of Cytology
1028:The Journal of Organic Chemistry
718:flavin-containing monooxygenases
637:There have been attempts to use
5114:Fiesselmann thiophene synthesis
4944:Westphalen–Lettré rearrangement
4924:Vinylcyclopropane rearrangement
4754:Kornblum–DeLaMare rearrangement
4399:Epoxidation of allylic alcohols
4309:Noyori asymmetric hydrogenation
4244:Kornblum–DeLaMare rearrangement
3919:Gallagher–Hollander degradation
5573:Chichibabin pyridine synthesis
5059:Chichibabin pyridine synthesis
5019:Blum–Ittah aziridine synthesis
4854:Ring expansion and contraction
3123:Cross dehydrogenative coupling
1663:Coordination Chemistry Reviews
1549:. Elsevier. pp. 671–688.
1200:Chemistry 206 (Fall 2006-2007)
730:cytochrome P450 monooxygenases
661:Baeyer-Villiger monooxygenases
433:and Gustav Pieper suggested a
281:of the migrating group to the
186:. The reaction is named after
1:
5543:Bischler–Napieralski reaction
5501:Heterocycle forming reactions
5154:Hemetsberger indole synthesis
5014:Bischler–Napieralski reaction
4929:Wagner–Meerwein rearrangement
4899:Sommelet–Hauser rearrangement
4879:Seyferth–Gilbert homologation
4744:Ireland–Claisen rearrangement
4739:Hofmann–Martius rearrangement
4499:2,3-sigmatropic rearrangement
4114:Corey–Winter olefin synthesis
4039:Barton–McCombie deoxygenation
3682:Corey–Winter olefin synthesis
3636:Seyferth–Gilbert homologation
3503:Seyferth–Gilbert homologation
2341:10.1016/S0040-4039(01)81819-0
2311:10.1016/S0040-4039(01)81818-9
1984:10.1016/S0074-7696(06)60002-8
1927:10.1016/j.jbiotec.2006.03.044
1730:Chemistry: A European Journal
1611:10.1016/S0040-4020(01)92726-7
218:protonates the oxygen of the
5648:Lehmstedt–Tanasescu reaction
5608:Gabriel–Colman rearrangement
5563:Bucherer carbazole synthesis
5558:Borsche–Drechsel cyclization
5538:Bernthsen acridine synthesis
5523:Bamberger triazine synthesis
5508:Algar–Flynn–Oyamada reaction
5219:Nazarov cyclization reaction
5084:De Kimpe aziridine synthesis
5039:Bucherer carbazole synthesis
5034:Borsche–Drechsel cyclization
4804:Nazarov cyclization reaction
4784:Meyer–Schuster rearrangement
4714:Gabriel–Colman rearrangement
4464:Wolffenstein–Böters reaction
4349:Reduction of nitro compounds
4199:Grundmann aldehyde synthesis
4004:Algar–Flynn–Oyamada reaction
3413:Olefin conversion technology
3408:Nozaki–Hiyama–Kishi reaction
3203:Gabriel–Colman rearrangement
3093:Claisen-Schmidt condensation
3038:Bouveault aldehyde synthesis
1196:"Stereoelectronic Effects-2"
174:from a cyclic ketone, using
5742:Organic oxidation reactions
5623:Hantzsch pyridine synthesis
5402:Enone–alkene cycloadditions
5224:Nenitzescu indole synthesis
5144:Hantzsch pyridine synthesis
5109:Ferrario–Ackermann reaction
4759:Kowalski ester homologation
4724:Halogen dance rearrangement
4569:Benzilic acid rearrangement
3994:Akabori amino-acid reaction
3954:Von Braun amide degradation
3899:Barbier–Wieland degradation
3851:Nenitzescu indole synthesis
3831:Kharasch–Sosnovsky reaction
3722:Julia–Kocienski olefination
3626:Kowalski ester homologation
3323:Kowalski ester homologation
3298:Julia–Kocienski olefination
3053:Cadiot–Chodkiewicz coupling
2978:Aza-Baylis–Hillman reaction
2923:Acetoacetic ester synthesis
2634:Dynamic binding (chemistry)
2624:Conrotatory and disrotatory
2599:Charge remote fragmentation
2358:Penicillium lanosocoeruleum
1286:10.1002/0471264180.or009.03
908:10.1002/0471264180.or043.03
746:three-dimensional structure
679:flavin adenine dinucleotide
409:There were three suggested
327:primary trend is observed.
316:Electron-withdrawing groups
5768:
5688:Robinson–Gabriel synthesis
5638:Kröhnke pyridine synthesis
5472:Retro-Diels–Alder reaction
5412:Imine Diels–Alder reaction
5199:Kröhnke pyridine synthesis
4814:Newman–Kwart rearrangement
4789:Mislow–Evans rearrangement
4699:Fischer–Hepp rearrangement
4644:Di-π-methane rearrangement
4424:Stephen aldehyde synthesis
4159:Eschweiler–Clarke reaction
3876:Williamson ether synthesis
3193:Fujiwara–Moritani reaction
3098:Combes quinoline synthesis
3063:Carbonyl olefin metathesis
2764:More O'Ferrall–Jencks plot
2689:Grunwald–Winstein equation
2659:Electron-withdrawing group
2594:Catalytic resonance theory
2377:10.3390/molecules181113812
2030:10.1021/acschembio.5b01016
1978:. Academic Press: 35–112.
1217:(4 ed.). p. 90.
458:William von Eggers Doering
35:Baeyer-Villiger oxidation
5698:Urech hydantoin synthesis
5678:Pomeranz–Fritsch reaction
5603:Fischer oxazole synthesis
5337:1,3-Dipolar cycloaddition
5309:Urech hydantoin synthesis
5279:Reissert indole synthesis
5264:Pomeranz–Fritsch reaction
5194:Knorr quinoline synthesis
5124:Fischer oxazole synthesis
5054:Camps quinoline synthesis
4974:1,3-Dipolar cycloaddition
4874:Semipinacol rearrangement
4849:Ramberg–Bäcklund reaction
4834:Piancatelli rearrangement
4774:McFadyen–Stevens reaction
4529:Alpha-ketol rearrangement
4284:McFadyen–Stevens reaction
4229:Kiliani–Fischer synthesis
4149:Elbs persulfate oxidation
4074:Bouveault–Blanc reduction
4034:Baeyer–Villiger oxidation
3866:Schotten–Baumann reaction
3742:Ramberg–Bäcklund reaction
3621:Kiliani–Fischer synthesis
3463:Ramberg–Bäcklund reaction
3448:Pinacol coupling reaction
3443:Piancatelli rearrangement
3338:Liebeskind–Srogl coupling
3188:Fujimoto–Belleau reaction
2905:List of organic reactions
2769:Negative hyperconjugation
2514:
2456:
1675:10.1016/j.ccr.2017.05.010
1256:10.1002/cber.189903203151
524:is correlated with lower
398:, and tetrahydrocarvone.
210:In the first step of the
201:Baeyer-Villiger oxidation
156:Baeyer–Villiger oxidation
148:
127:baeyer-villiger-oxidation
122:Organic Chemistry Portal
116:
105:
96:
79:
72:
63:
34:
18:Baeyer-Villiger oxidation
5747:Esterification reactions
5673:Pictet–Spengler reaction
5588:Einhorn–Brunner reaction
5553:Boger pyridine synthesis
5447:Oxo-Diels–Alder reaction
5362:Aza-Diels–Alder reaction
5259:Pictet–Spengler reaction
5159:Hofmann–Löffler reaction
5149:Hegedus indole synthesis
5119:Fischer indole synthesis
4994:Bartoli indole synthesis
4949:Willgerodt rearrangement
4779:McLafferty rearrangement
4689:Ferrier carbocyclization
4504:2,3-Wittig rearrangement
4494:1,2-Wittig rearrangement
4334:Parikh–Doering oxidation
4324:Oxygen rebound mechanism
3989:Adkins–Peterson reaction
3881:Yamaguchi esterification
3821:Hegedus indole synthesis
3786:Bartoli indole synthesis
3657:Bamford–Stevens reaction
3573:Weinreb ketone synthesis
3533:Stork enamine alkylation
3308:Knoevenagel condensation
3178:Ferrier carbocyclization
3068:Castro–Stephens coupling
2694:Hammett acidity function
2684:Free-energy relationship
2629:Curtin–Hammett principle
2614:Conformational isomerism
2114:10.1021/acscatal.8b03793
2081:10.1021/acscatal.9b03396
1915:Journal of Biotechnology
639:organometallic catalysts
553:tert-butyl hydroperoxide
306:Stereoelectronic effects
271:stereoelectronic effects
5737:Organic redox reactions
5633:Knorr pyrrole synthesis
5568:Bucherer–Bergs reaction
5513:Allan–Robinson reaction
5492:Wagner-Jauregg reaction
5284:Ring-closing metathesis
5209:Larock indole synthesis
5189:Knorr pyrrole synthesis
5044:Bucherer–Bergs reaction
4909:Stieglitz rearrangement
4889:Skattebøl rearrangement
4859:Ring-closing metathesis
4719:Group transfer reaction
4684:Favorskii rearrangement
4624:Cornforth rearrangement
4554:Bamberger rearrangement
4459:Wolff–Kishner reduction
4279:Markó–Lam deoxygenation
4174:Fleming–Tamao oxidation
4169:Fischer–Tropsch process
3856:Oxymercuration reaction
3836:Knorr pyrrole synthesis
3662:Barton–Kellogg reaction
3568:Wagner-Jauregg reaction
3488:Ring-closing metathesis
3478:Reimer–Tiemann reaction
3468:Rauhut–Currier reaction
3383:Nef isocyanide reaction
3343:Malonic ester synthesis
3313:Knorr pyrrole synthesis
3248:High dilution principle
3183:Friedel–Crafts reaction
3118:Cross-coupling reaction
3043:Bucherer–Bergs reaction
3028:Blanc chloromethylation
3018:Blaise ketone synthesis
2993:Baylis–Hillman reaction
2988:Barton–Kellogg reaction
2963:Allan–Robinson reaction
2869:Woodward–Hoffmann rules
2604:Charge-transfer complex
2354:Świzdor, Alina (2013).
1690:Chemical Communications
518:trifluoroperacetic acid
388:peroxymonosulfuric acid
5598:Feist–Benary synthesis
5372:Bradsher cycloaddition
5342:4+4 Photocycloaddition
5299:Simmons–Smith reaction
5244:Paternò–Büchi reaction
5104:Feist–Benary synthesis
5094:Dieckmann condensation
4844:Pummerer rearrangement
4824:Oxy-Cope rearrangement
4799:Myers allene synthesis
4749:Jacobsen rearrangement
4664:Electrocyclic reaction
4639:Demjanov rearrangement
4594:Buchner ring expansion
4564:Beckmann rearrangement
4544:Aza-Cope rearrangement
4539:Arndt–Eistert reaction
4514:Alkyne zipper reaction
4434:Transfer hydrogenation
4409:Sharpless oxyamination
4384:Selenoxide elimination
4269:Lombardo methylenation
4194:Griesbaum coozonolysis
4104:Corey–Itsuno reduction
4079:Boyland–Sims oxidation
4019:Angeli–Rimini reaction
3667:Boord olefin synthesis
3611:Arndt–Eistert reaction
3603:Homologation reactions
3403:Nitro-Mannich reaction
3318:Kolbe–Schmitt reaction
3128:Cross-coupling partner
3048:Buchner ring expansion
2968:Arndt–Eistert reaction
2734:Kinetic isotope effect
2481:Rearrangement reaction
1512:10.1002/anie.201505648
1477:10.1002/cctc.201000088
810:
800:dehydroepiandrosterone
787:
670:
611:
514:-chloroperbenzoic acid
481:
453:
406:
355:
335:
307:
266:
202:
58:Organic redox reaction
5457:Pauson–Khand reaction
5294:Sharpless epoxidation
5249:Pechmann condensation
5129:Friedländer synthesis
5079:Davis–Beirut reaction
4934:Wallach rearrangement
4904:Stevens rearrangement
4839:Pinacol rearrangement
4819:Overman rearrangement
4734:Hofmann rearrangement
4729:Hayashi rearrangement
4694:Ferrier rearrangement
4649:Dimroth rearrangement
4634:Curtius rearrangement
4629:Criegee rearrangement
4609:Claisen rearrangement
4599:Carroll rearrangement
4534:Amadori rearrangement
4524:Allylic rearrangement
4404:Sharpless epoxidation
4139:Dess–Martin oxidation
4064:Bohn–Schmidt reaction
3924:Hofmann rearrangement
3727:Kauffmann olefination
3650:Olefination reactions
3588:Wurtz–Fittig reaction
3423:Palladium–NHC complex
3303:Kauffmann olefination
3258:Homologation reaction
3108:Corey–House synthesis
3088:Claisen rearrangement
2884:Yukawa–Tsuno equation
2844:Swain–Lupton equation
2824:Spherical aromaticity
2759:Möbius–Hückel concept
2544:Aromatic ring current
2506:Substitution reaction
1244:Ber. Dtsch. Chem. Ges
1213:Sanyal, S.N. (2003).
1015:. Harvard University.
808:
785:
668:
657:compounds, followed.
609:
479:
451:
404:
382:Historical background
353:
333:
305:
289:on the oxygen of the
264:
244:rate determining step
200:
5663:Paal–Knorr synthesis
5533:Barton–Zard reaction
5477:Staudinger synthesis
5427:Ketene cycloaddition
5397:Diels–Alder reaction
5377:Cheletropic reaction
5357:Alkyne trimerisation
5239:Paal–Knorr synthesis
5204:Kulinkovich reaction
5179:Jacobsen epoxidation
5099:Diels–Alder reaction
4894:Smiles rearrangement
4884:Sigmatropic reaction
4769:Lossen rearrangement
4619:Corey–Fuchs reaction
4584:Boekelheide reaction
4579:Bergmann degradation
4509:Achmatowicz reaction
4294:Methionine sulfoxide
4094:Clemmensen reduction
4054:Bergmann degradation
3984:Acyloin condensation
3949:Strecker degradation
3904:Bergmann degradation
3871:Ullmann condensation
3737:Peterson olefination
3712:Hydrazone iodination
3692:Elimination reaction
3593:Zincke–Suhl reaction
3513:Sonogashira coupling
3473:Reformatsky reaction
3433:Peterson olefination
3398:Nierenstein reaction
3328:Kulinkovich reaction
3143:Diels–Alder reaction
3103:Corey–Fuchs reaction
3083:Claisen condensation
2953:Alkyne trimerisation
2928:Acyloin condensation
2894:Σ-bishomoaromaticity
2854:Thorpe–Ingold effect
2466:Elimination reaction
2223:10.1021/jacs.8b04742
2018:ACS Chemical Biology
968:Angew. Chem. Int. Ed
443:Criegee intermediate
429:intermediate, while
224:Criegee intermediate
5683:Prilezhaev reaction
5668:Pellizzari reaction
5347:(4+3) cycloaddition
5314:Van Leusen reaction
5289:Robinson annulation
5274:Pschorr cyclization
5269:Prilezhaev reaction
4999:Bergman cyclization
4954:Wolff rearrangement
4939:Weerman degradation
4829:Pericyclic reaction
4809:Neber rearrangement
4704:Fries rearrangement
4589:Brook rearrangement
4574:Bergman cyclization
4419:Staudinger reaction
4364:Rosenmund reduction
4354:Reductive amination
4319:Oppenauer oxidation
4109:Corey–Kim oxidation
4084:Cannizzaro reaction
3959:Weerman degradation
3934:Isosaccharinic acid
3846:Mukaiyama hydration
3702:Hofmann elimination
3687:Dehydrohalogenation
3672:Chugaev elimination
3493:Robinson annulation
3438:Pfitzinger reaction
3208:Gattermann reaction
3153:Wulff–Dötz reaction
3133:Dakin–West reaction
3058:Carbonyl allylation
3003:Bergman cyclization
2789:Kennedy J. P. Orton
2709:Hammond's postulate
2679:Flippin–Lodge angle
2649:Electromeric effect
2574:Beta-silicon effect
2559:Baker–Nathan effect
2370:(11): 13812–13822.
2281:10.1021/ja00506a057
2217:(33): 10464–10472.
2107:(12): 11648–11656.
2074:(12): 11207–11241.
1831:(37): 11156–11167.
1506:(40): 11848–11851.
1449:10.1021/ja01158a062
1422:10.1021/ja01158a061
1395:10.1021/ja01168a041
1361:10.1021/ja01118a035
1141:10.1021/ja01556a057
411:reaction mechanisms
324:resonance structure
228:concerted mechanism
5432:McCormack reaction
5382:Conia-ene reaction
5214:Madelung synthesis
5004:Biginelli reaction
4794:Mumm rearrangement
4679:Favorskii reaction
4614:Cope rearrangement
4604:Chan rearrangement
4369:Rubottom oxidation
4299:Miyaura borylation
4264:Lipid peroxidation
4259:Lindgren oxidation
4239:Kornblum oxidation
4234:Kolbe electrolysis
4179:Fukuyama reduction
4089:Carbonyl reduction
3939:Marker degradation
3801:Diazonium compound
3791:Boudouard reaction
3770:Carbon-heteroatom
3697:Grieco elimination
3483:Rieche formylation
3428:Passerini reaction
3358:Meerwein arylation
3278:Hydroxymethylation
3173:Favorskii reaction
3073:Chan rearrangement
3008:Biginelli reaction
2933:Aldol condensation
2779:2-Norbornyl cation
2754:Möbius aromaticity
2749:Markovnikov's rule
2644:Effective molarity
2589:Bürgi–Dunitz angle
2579:Bicycloaromaticity
2265:Montanoa tomentosa
1068:ten Brink, G.-J.;
811:
788:
750:enzyme engineering
671:
612:
482:
454:
407:
356:
344:gauche interaction
336:
308:
267:
212:reaction mechanism
206:Reaction mechanism
203:
5724:
5723:
5720:
5719:
5716:
5715:
5708:Wohl–Aue reaction
5352:6+4 Cycloaddition
5169:Iodolactonization
4489:1,2-rearrangement
4454:Wohl–Aue reaction
4374:Sabatier reaction
4339:Pinnick oxidation
4304:Mozingo reduction
4249:Leuckart reaction
4204:Haloform reaction
4119:Criegee oxidation
4099:Collins oxidation
4049:Benkeser reaction
4044:Bechamp reduction
4014:Andrussow process
3999:Alcohol oxidation
3909:Edman degradation
3816:Haloform reaction
3765:
3764:
3752:Takai olefination
3717:Julia olefination
3543:Takai olefination
3418:Olefin metathesis
3293:Julia olefination
3218:Grignard reaction
3198:Fukuyama coupling
3113:Coupling reaction
3078:Chan–Lam coupling
2948:Alkyne metathesis
2943:Alkane metathesis
2799:Phosphaethynolate
2704:George S. Hammond
2664:Electronic effect
2619:Conjugated system
2501:Stereospecificity
2496:Stereoselectivity
2461:Addition reaction
2450:organic reactions
2335:(32): 3031–3034.
2305:(32): 3027–3030.
2275:(12): 3405–3407.
2165:10.1002/bit.27022
1880:10.1021/ja2103839
1837:10.1021/bi011153h
1794:10.1021/cr1003437
1639:10.1021/jo0057710
1556:978-0-08-035930-4
1471:(10): 1296–1302.
1389:(12): 5515–5518.
1355:(22): 5595–5598.
1311:Eur. J. Org. Chem
1274:Organic Reactions
1224:978-81-7709-605-7
1173:978-0-393-93149-5
1158:Organic Chemistry
1135:(23): 6393–6398.
1086:10.1021/cr030011l
1040:10.1021/jo0626562
1008:Myers, Andrew G.
974:(16): 2851–2855.
896:Organic Reactions
875:978-0-12-369483-6
581:functional groups
549:hydrogen peroxide
254:ion produces the
152:
151:
112:
111:
16:(Redirected from
5759:
5703:Wenker synthesis
5693:Stollé synthesis
5548:Bobbitt reaction
5518:Auwers synthesis
5462:Povarov reaction
5387:Cyclopropanation
5325:
5319:Wenker synthesis
5074:Darzens reaction
5024:Bobbitt reaction
4869:Schmidt reaction
4674:Enyne metathesis
4449:Whiting reaction
4444:Wharton reaction
4389:Shapiro reaction
4379:Sarett oxidation
4344:Prévost reaction
4154:Emde degradation
3964:Wohl degradation
3944:Ruff degradation
3914:Emde degradation
3811:Grignard reagent
3747:Shapiro reaction
3732:McMurry reaction
3599:
3563:Ullmann reaction
3528:Stollé synthesis
3518:Stetter reaction
3508:Shapiro reaction
3498:Sakurai reaction
3393:Negishi coupling
3373:Minisci reaction
3368:Michael reaction
3353:McMurry reaction
3348:Mannich reaction
3228:Hammick reaction
3223:Grignard reagent
3163:Enyne metathesis
3148:Doebner reaction
3138:Darzens reaction
2983:Barbier reaction
2973:Auwers synthesis
2900:
2874:Woodward's rules
2839:Superaromaticity
2829:Spiroaromaticity
2729:Inductive effect
2724:Hyperconjugation
2699:Hammett equation
2639:Edwards equation
2491:Regioselectivity
2442:
2435:
2428:
2419:
2400:
2399:
2389:
2379:
2351:
2345:
2344:
2329:Tetrahedron Lett
2324:
2315:
2314:
2299:Tetrahedron Lett
2294:
2285:
2284:
2269:J. Am. Chem. Soc
2259:
2253:
2252:
2242:
2202:
2196:
2195:
2185:
2167:
2158:(9): 2167–2177.
2143:
2137:
2136:
2126:
2116:
2092:
2086:
2085:
2083:
2059:
2050:
2049:
2024:(4): 1039–1048.
2012:
2006:
2005:
1963:
1957:
1956:
1938:
1906:
1900:
1899:
1874:(5): 2732–2741.
1863:
1857:
1856:
1820:
1814:
1813:
1788:(7): 4165–4222.
1782:Chemical Reviews
1773:
1762:
1761:
1724:
1718:
1717:
1698:10.1039/B105927K
1685:
1679:
1678:
1657:
1651:
1650:
1633:(7): 2429–2433.
1621:
1615:
1614:
1594:
1588:
1587:
1584:scs.illinois.edu
1581:
1575:Seymour, Craig.
1572:
1561:
1560:
1537:
1524:
1523:
1495:
1489:
1488:
1459:
1453:
1452:
1437:J. Am. Chem. Soc
1432:
1426:
1425:
1410:J. Am. Chem. Soc
1405:
1399:
1398:
1378:
1365:
1364:
1349:J. Am. Chem. Soc
1344:
1327:
1326:
1306:
1300:
1299:
1269:
1260:
1259:
1250:(3): 3625–3633.
1235:
1229:
1228:
1210:
1204:
1203:
1191:
1178:
1177:
1161:
1151:
1145:
1144:
1129:J. Am. Chem. Soc
1124:
1113:
1112:
1104:
1098:
1097:
1080:(9): 4105–4123.
1070:Arends, W. C. E.
1065:
1052:
1051:
1034:(8): 3031–3041.
1023:
1017:
1016:
1014:
1005:
992:
991:
963:
950:
949:
931:
922:
921:
891:
880:
879:
863:
853:
699:molecular oxygen
643:enantioselective
340:transition state
188:Adolf von Baeyer
160:organic reaction
144:
129:
107:Ester or Lactone
100:
70:
69:
44:Adolf von Baeyer
32:
27:Organic reaction
21:
5767:
5766:
5762:
5761:
5760:
5758:
5757:
5756:
5727:
5726:
5725:
5712:
5613:Gewald reaction
5496:
5323:
5304:Skraup reaction
5139:Graham reaction
5134:Gewald reaction
4965:
4958:
4480:
4473:
4429:Swern oxidation
4414:Stahl oxidation
4359:Riley oxidation
4314:Omega oxidation
4274:Luche reduction
4224:Jones oxidation
4189:Glycol cleavage
4184:Ganem oxidation
4129:Davis oxidation
4124:Dakin oxidation
4059:Birch reduction
4009:Amide reduction
3975:
3968:
3929:Hooker reaction
3891:
3885:
3773:
3771:
3761:
3757:Wittig reaction
3645:
3641:Wittig reaction
3616:Hooker reaction
3597:
3578:Wittig reaction
3553:Thorpe reaction
3538:Suzuki reaction
3523:Stille reaction
3458:Quelet reaction
3333:Kumada coupling
3283:Ivanov reaction
3273:Hydrovinylation
3253:Hiyama coupling
3213:Glaser coupling
3023:Blaise reaction
3013:Bingel reaction
2998:Benary reaction
2915:
2913:
2907:
2898:
2794:Passive binding
2714:Homoaromaticity
2564:Baldwin's rules
2539:Antiaromaticity
2534:Anomeric effect
2510:
2452:
2446:
2409:
2404:
2403:
2353:
2352:
2348:
2326:
2325:
2318:
2296:
2295:
2288:
2261:
2260:
2256:
2204:
2203:
2199:
2145:
2144:
2140:
2094:
2093:
2089:
2061:
2060:
2053:
2014:
2013:
2009:
1994:
1965:
1964:
1960:
1908:
1907:
1903:
1865:
1864:
1860:
1822:
1821:
1817:
1775:
1774:
1765:
1736:(20): 4708–17.
1726:
1725:
1721:
1687:
1686:
1682:
1659:
1658:
1654:
1623:
1622:
1618:
1596:
1595:
1591:
1579:
1574:
1573:
1564:
1557:
1539:
1538:
1527:
1497:
1496:
1492:
1461:
1460:
1456:
1434:
1433:
1429:
1407:
1406:
1402:
1380:
1379:
1368:
1346:
1345:
1330:
1308:
1307:
1303:
1296:
1271:
1270:
1263:
1237:
1236:
1232:
1225:
1212:
1211:
1207:
1193:
1192:
1181:
1174:
1153:
1152:
1148:
1126:
1125:
1116:
1106:
1105:
1101:
1067:
1066:
1055:
1025:
1024:
1020:
1012:
1007:
1006:
995:
965:
964:
953:
946:
933:
932:
925:
918:
893:
892:
883:
876:
855:
854:
833:
828:
816:
793:
772:
767:
754:thermostability
687:catalytic cycle
663:
635:
622:
617:
565:
529:
503:
495:stereoretentive
491:stereochemistry
487:
485:Stereochemistry
384:
377:
373:
369:
365:
361:
240:carboxylic acid
208:
192:Victor Villiger
140:
125:
98:
86:
81:
48:Victor Villiger
46:
28:
23:
22:
15:
12:
11:
5:
5765:
5763:
5755:
5754:
5752:Name reactions
5749:
5744:
5739:
5729:
5728:
5722:
5721:
5718:
5717:
5714:
5713:
5711:
5710:
5705:
5700:
5695:
5690:
5685:
5680:
5675:
5670:
5665:
5660:
5655:
5650:
5645:
5640:
5635:
5630:
5625:
5620:
5618:Hantzsch ester
5615:
5610:
5605:
5600:
5595:
5590:
5585:
5580:
5575:
5570:
5565:
5560:
5555:
5550:
5545:
5540:
5535:
5530:
5528:Banert cascade
5525:
5520:
5515:
5510:
5504:
5502:
5498:
5497:
5495:
5494:
5489:
5484:
5479:
5474:
5469:
5467:Prato reaction
5464:
5459:
5454:
5449:
5444:
5439:
5434:
5429:
5424:
5419:
5414:
5409:
5404:
5399:
5394:
5389:
5384:
5379:
5374:
5369:
5364:
5359:
5354:
5349:
5344:
5339:
5333:
5331:
5322:
5321:
5316:
5311:
5306:
5301:
5296:
5291:
5286:
5281:
5276:
5271:
5266:
5261:
5256:
5251:
5246:
5241:
5236:
5231:
5226:
5221:
5216:
5211:
5206:
5201:
5196:
5191:
5186:
5181:
5176:
5171:
5166:
5161:
5156:
5151:
5146:
5141:
5136:
5131:
5126:
5121:
5116:
5111:
5106:
5101:
5096:
5091:
5086:
5081:
5076:
5071:
5066:
5061:
5056:
5051:
5046:
5041:
5036:
5031:
5026:
5021:
5016:
5011:
5006:
5001:
4996:
4991:
4986:
4981:
4976:
4970:
4968:
4960:
4959:
4957:
4956:
4951:
4946:
4941:
4936:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4866:
4861:
4856:
4851:
4846:
4841:
4836:
4831:
4826:
4821:
4816:
4811:
4806:
4801:
4796:
4791:
4786:
4781:
4776:
4771:
4766:
4761:
4756:
4751:
4746:
4741:
4736:
4731:
4726:
4721:
4716:
4711:
4706:
4701:
4696:
4691:
4686:
4681:
4676:
4671:
4666:
4661:
4656:
4651:
4646:
4641:
4636:
4631:
4626:
4621:
4616:
4611:
4606:
4601:
4596:
4591:
4586:
4581:
4576:
4571:
4566:
4561:
4559:Banert cascade
4556:
4551:
4546:
4541:
4536:
4531:
4526:
4521:
4516:
4511:
4506:
4501:
4496:
4491:
4485:
4483:
4479:Rearrangement
4475:
4474:
4472:
4471:
4469:Zinin reaction
4466:
4461:
4456:
4451:
4446:
4441:
4439:Wacker process
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:
4214:Hydrogenolysis
4211:
4206:
4201:
4196:
4191:
4186:
4181:
4176:
4171:
4166:
4164:Étard reaction
4161:
4156:
4151:
4146:
4141:
4136:
4131:
4126:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4069:Bosch reaction
4066:
4061:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3980:
3978:
3974:Organic redox
3970:
3969:
3967:
3966:
3961:
3956:
3951:
3946:
3941:
3936:
3931:
3926:
3921:
3916:
3911:
3906:
3901:
3895:
3893:
3887:
3886:
3884:
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3806:Esterification
3803:
3798:
3793:
3788:
3783:
3777:
3775:
3767:
3766:
3763:
3762:
3760:
3759:
3754:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3714:
3709:
3704:
3699:
3694:
3689:
3684:
3679:
3674:
3669:
3664:
3659:
3653:
3651:
3647:
3646:
3644:
3643:
3638:
3633:
3628:
3623:
3618:
3613:
3607:
3605:
3596:
3595:
3590:
3585:
3583:Wurtz reaction
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3455:
3453:Prins reaction
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:
3268:Hydrocyanation
3265:
3260:
3255:
3250:
3245:
3240:
3238:Henry reaction
3235:
3230:
3225:
3220:
3215:
3210:
3205:
3200:
3195:
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:
2938:Aldol reaction
2935:
2930:
2925:
2919:
2917:
2912:Carbon-carbon
2909:
2908:
2903:
2897:
2896:
2891:
2889:Zaitsev's rule
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2834:Steric effects
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2726:
2721:
2716:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2676:
2671:
2666:
2661:
2656:
2651:
2646:
2641:
2636:
2631:
2626:
2621:
2616:
2611:
2606:
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2531:
2526:
2521:
2515:
2512:
2511:
2509:
2508:
2503:
2498:
2493:
2488:
2486:Redox reaction
2483:
2478:
2473:
2471:Polymerization
2468:
2463:
2457:
2454:
2453:
2447:
2445:
2444:
2437:
2430:
2422:
2416:
2415:
2408:
2407:External links
2405:
2402:
2401:
2346:
2316:
2286:
2254:
2197:
2138:
2087:
2051:
2007:
1992:
1958:
1921:(4): 670–689.
1901:
1858:
1815:
1763:
1719:
1692:(21): 2190–1.
1680:
1652:
1616:
1605:(6): 763–765.
1589:
1562:
1555:
1525:
1490:
1454:
1443:(2): 882–885.
1427:
1416:(2): 878–882.
1400:
1366:
1328:
1317:(4): 737–750.
1301:
1294:
1261:
1230:
1223:
1205:
1179:
1172:
1146:
1114:
1099:
1053:
1018:
993:
951:
945:978-0387683546
944:
923:
916:
902:(3): 251–798.
881:
874:
830:
829:
827:
824:
823:
822:
820:Dakin reaction
815:
812:
792:
789:
771:
768:
766:
763:
724:system of the
722:detoxification
662:
659:
634:
631:
621:
618:
616:
613:
564:
561:
545:peracetic acid
541:performic acid
527:
502:
499:
486:
483:
464:-labelling of
439:Rudolf Criegee
419:carbonyl group
383:
380:
375:
371:
367:
363:
359:
275:antiperiplanar
236:peroxide group
220:carbonyl group
207:
204:
162:that forms an
150:
149:
146:
145:
138:
131:
130:
123:
119:
118:
114:
113:
110:
109:
103:
102:
94:
93:
84:
77:
76:
66:
65:
61:
60:
55:
54:Reaction type
51:
50:
41:
37:
36:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5764:
5753:
5750:
5748:
5745:
5743:
5740:
5738:
5735:
5734:
5732:
5709:
5706:
5704:
5701:
5699:
5696:
5694:
5691:
5689:
5686:
5684:
5681:
5679:
5676:
5674:
5671:
5669:
5666:
5664:
5661:
5659:
5656:
5654:
5651:
5649:
5646:
5644:
5641:
5639:
5636:
5634:
5631:
5629:
5628:Herz reaction
5626:
5624:
5621:
5619:
5616:
5614:
5611:
5609:
5606:
5604:
5601:
5599:
5596:
5594:
5591:
5589:
5586:
5584:
5581:
5579:
5576:
5574:
5571:
5569:
5566:
5564:
5561:
5559:
5556:
5554:
5551:
5549:
5546:
5544:
5541:
5539:
5536:
5534:
5531:
5529:
5526:
5524:
5521:
5519:
5516:
5514:
5511:
5509:
5506:
5505:
5503:
5499:
5493:
5490:
5488:
5485:
5483:
5480:
5478:
5475:
5473:
5470:
5468:
5465:
5463:
5460:
5458:
5455:
5453:
5450:
5448:
5445:
5443:
5440:
5438:
5435:
5433:
5430:
5428:
5425:
5423:
5420:
5418:
5415:
5413:
5410:
5408:
5405:
5403:
5400:
5398:
5395:
5393:
5390:
5388:
5385:
5383:
5380:
5378:
5375:
5373:
5370:
5368:
5365:
5363:
5360:
5358:
5355:
5353:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5334:
5332:
5330:
5329:Cycloaddition
5326:
5320:
5317:
5315:
5312:
5310:
5307:
5305:
5302:
5300:
5297:
5295:
5292:
5290:
5287:
5285:
5282:
5280:
5277:
5275:
5272:
5270:
5267:
5265:
5262:
5260:
5257:
5255:
5252:
5250:
5247:
5245:
5242:
5240:
5237:
5235:
5232:
5230:
5227:
5225:
5222:
5220:
5217:
5215:
5212:
5210:
5207:
5205:
5202:
5200:
5197:
5195:
5192:
5190:
5187:
5185:
5182:
5180:
5177:
5175:
5174:Isay reaction
5172:
5170:
5167:
5165:
5162:
5160:
5157:
5155:
5152:
5150:
5147:
5145:
5142:
5140:
5137:
5135:
5132:
5130:
5127:
5125:
5122:
5120:
5117:
5115:
5112:
5110:
5107:
5105:
5102:
5100:
5097:
5095:
5092:
5090:
5087:
5085:
5082:
5080:
5077:
5075:
5072:
5070:
5069:Cycloaddition
5067:
5065:
5062:
5060:
5057:
5055:
5052:
5050:
5047:
5045:
5042:
5040:
5037:
5035:
5032:
5030:
5027:
5025:
5022:
5020:
5017:
5015:
5012:
5010:
5007:
5005:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4980:
4977:
4975:
4972:
4971:
4969:
4967:
4964:Ring forming
4961:
4955:
4952:
4950:
4947:
4945:
4942:
4940:
4937:
4935:
4932:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4864:Rupe reaction
4862:
4860:
4857:
4855:
4852:
4850:
4847:
4845:
4842:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4820:
4817:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4787:
4785:
4782:
4780:
4777:
4775:
4772:
4770:
4767:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4735:
4732:
4730:
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4650:
4647:
4645:
4642:
4640:
4637:
4635:
4632:
4630:
4627:
4625:
4622:
4620:
4617:
4615:
4612:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4592:
4590:
4587:
4585:
4582:
4580:
4577:
4575:
4572:
4570:
4567:
4565:
4562:
4560:
4557:
4555:
4552:
4550:
4547:
4545:
4542:
4540:
4537:
4535:
4532:
4530:
4527:
4525:
4522:
4520:
4517:
4515:
4512:
4510:
4507:
4505:
4502:
4500:
4497:
4495:
4492:
4490:
4487:
4486:
4484:
4482:
4476:
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:
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:
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4265:
4262:
4260:
4257:
4255:
4254:Ley oxidation
4252:
4250:
4247:
4245:
4242:
4240:
4237:
4235:
4232:
4230:
4227:
4225:
4222:
4220:
4219:Hydroxylation
4217:
4215:
4212:
4210:
4209:Hydrogenation
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4160:
4157:
4155:
4152:
4150:
4147:
4145:
4144:DNA oxidation
4142:
4140:
4137:
4135:
4134:Deoxygenation
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4024:Aromatization
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3981:
3979:
3977:
3971:
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:
3896:
3894:
3888:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3862:
3861:Reed reaction
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3778:
3776:
3772:bond forming
3768:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3703:
3700:
3698:
3695:
3693:
3690:
3688:
3685:
3683:
3680:
3678:
3677:Cope reaction
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3658:
3655:
3654:
3652:
3648:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3614:
3612:
3609:
3608:
3606:
3604:
3600:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
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:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3388:Nef synthesis
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3364:
3363:Methylenation
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
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:
3233:Heck reaction
3231:
3229:
3226:
3224:
3221:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
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:
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:
2920:
2918:
2914:bond forming
2910:
2906:
2901:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2879:Y-aromaticity
2877:
2875:
2872:
2870:
2867:
2865:
2864:Walsh diagram
2862:
2860:
2857:
2855:
2852:
2850:
2849:Taft equation
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2819:Σ-aromaticity
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2747:
2745:
2744:Marcus theory
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2720:
2719:Hückel's rule
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2674:Evelyn effect
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2654:Electron-rich
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2569:Bema Hapothle
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2516:
2513:
2507:
2504:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2467:
2464:
2462:
2459:
2458:
2455:
2451:
2443:
2438:
2436:
2431:
2429:
2424:
2423:
2420:
2414:
2411:
2410:
2406:
2397:
2393:
2388:
2383:
2378:
2373:
2369:
2365:
2361:
2359:
2350:
2347:
2342:
2338:
2334:
2330:
2323:
2321:
2317:
2312:
2308:
2304:
2300:
2293:
2291:
2287:
2282:
2278:
2274:
2270:
2266:
2258:
2255:
2250:
2246:
2241:
2236:
2232:
2228:
2224:
2220:
2216:
2212:
2208:
2201:
2198:
2193:
2189:
2184:
2179:
2175:
2171:
2166:
2161:
2157:
2153:
2149:
2142:
2139:
2134:
2130:
2125:
2120:
2115:
2110:
2106:
2102:
2101:ACS Catalysis
2098:
2091:
2088:
2082:
2077:
2073:
2069:
2068:ACS Catalysis
2065:
2058:
2056:
2052:
2047:
2043:
2039:
2035:
2031:
2027:
2023:
2019:
2011:
2008:
2003:
1999:
1995:
1993:9780123741141
1989:
1985:
1981:
1977:
1973:
1969:
1962:
1959:
1954:
1950:
1946:
1942:
1937:
1932:
1928:
1924:
1920:
1916:
1912:
1905:
1902:
1897:
1893:
1889:
1885:
1881:
1877:
1873:
1869:
1862:
1859:
1854:
1850:
1846:
1842:
1838:
1834:
1830:
1826:
1819:
1816:
1811:
1807:
1803:
1799:
1795:
1791:
1787:
1783:
1779:
1772:
1770:
1768:
1764:
1759:
1755:
1751:
1747:
1743:
1739:
1735:
1731:
1723:
1720:
1715:
1711:
1707:
1703:
1699:
1695:
1691:
1684:
1681:
1676:
1672:
1668:
1664:
1656:
1653:
1648:
1644:
1640:
1636:
1632:
1628:
1620:
1617:
1612:
1608:
1604:
1600:
1593:
1590:
1585:
1578:
1571:
1569:
1567:
1563:
1558:
1552:
1548:
1547:
1542:
1541:Grant R. Krow
1536:
1534:
1532:
1530:
1526:
1521:
1517:
1513:
1509:
1505:
1501:
1494:
1491:
1486:
1482:
1478:
1474:
1470:
1466:
1458:
1455:
1450:
1446:
1442:
1438:
1431:
1428:
1423:
1419:
1415:
1411:
1404:
1401:
1396:
1392:
1388:
1384:
1377:
1375:
1373:
1371:
1367:
1362:
1358:
1354:
1350:
1343:
1341:
1339:
1337:
1335:
1333:
1329:
1324:
1320:
1316:
1312:
1305:
1302:
1297:
1291:
1287:
1283:
1280:(3): 73–106.
1279:
1275:
1268:
1266:
1262:
1257:
1253:
1249:
1245:
1241:
1234:
1231:
1226:
1220:
1216:
1209:
1206:
1201:
1197:
1194:Evans, D. A.
1190:
1188:
1186:
1184:
1180:
1175:
1169:
1165:
1160:
1159:
1150:
1147:
1142:
1138:
1134:
1130:
1123:
1121:
1119:
1115:
1110:
1103:
1100:
1095:
1091:
1087:
1083:
1079:
1075:
1071:
1064:
1062:
1060:
1058:
1054:
1049:
1045:
1041:
1037:
1033:
1029:
1022:
1019:
1011:
1004:
1002:
1000:
998:
994:
989:
985:
981:
977:
973:
969:
962:
960:
958:
956:
952:
947:
941:
937:
930:
928:
924:
919:
913:
909:
905:
901:
897:
890:
888:
886:
882:
877:
871:
867:
862:
861:
852:
850:
848:
846:
844:
842:
840:
838:
836:
832:
825:
821:
818:
817:
813:
807:
803:
801:
798:
790:
784:
780:
778:
769:
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42:
39:
38:
33:
30:
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4669:Ene reaction
4033:
4029:Autoxidation
3890:Degradation
3781:Azo coupling
3558:Ugi reaction
3158:Ene reaction
2958:Alkynylation
2809:Polyfluorene
2804:Polar effect
2669:Electrophile
2584:Bredt's rule
2554:Baird's rule
2524:Alpha effect
2367:
2363:
2357:
2349:
2332:
2328:
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2100:
2090:
2071:
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2021:
2017:
2010:
1975:
1971:
1961:
1918:
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1828:
1825:Biochemistry
1824:
1818:
1785:
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1729:
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1630:
1627:J. Org. Chem
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737:biocatalysts
734:
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672:
636:
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566:
516:(mCPBA) and
511:
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488:
470:alkoxy group
466:benzophenone
455:
431:Georg Wittig
408:
385:
357:
337:
309:
294:
268:
252:oxocarbenium
226:. Through a
209:
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153:
142:RXNO:0000031
137:ontology ID
117:Identifiers
106:
97:
73:
40:Named after
29:
3168:Ethenolysis
2814:Ring strain
2784:Nucleophile
2609:Clar's rule
2549:Aromaticity
1669:: 220–255.
1599:Tetrahedron
1465:ChemCatChem
759:active site
693:equivalent
673:In nature,
641:to perform
569:peroxyacids
567:The use of
563:Limitations
321:carbocation
283:𝛔* orbital
246:. Finally,
176:peroxyacids
5731:Categories
5452:Ozonolysis
4979:Annulation
4329:Ozonolysis
2448:Topics in
2263:Zoapatle (
1295:0471264180
917:0471264180
826:References
770:Zoapatanol
728:along the
711:eliminates
522:reactivity
415:peroxyacid
279:𝛔 orbital
216:peroxyacid
4966:reactions
4481:reactions
3976:reactions
3892:reactions
3774:reactions
2916:reactions
2364:Molecules
2231:0002-7863
2174:1097-0290
2038:1554-8929
1945:0168-1656
1888:0002-7863
1845:0006-2960
1802:0009-2665
1750:1521-3765
1706:1364-548X
1074:Chem. Rev
703:substrate
685:. In the
647:prochiral
579:of other
577:oxidation
573:peroxides
462:oxygen-18
456:In 1953,
427:dioxirane
296:in silico
287:lone pair
180:peroxides
64:Reaction
2859:Vinylogy
2529:Annulene
2476:Reagents
2396:24213656
2249:30044629
2192:31124128
2133:30687578
2046:26771671
2002:17482904
1953:16712999
1896:22239272
1853:11551214
1810:21542563
1758:12561111
1714:12240094
1647:11281784
1520:26267787
1485:98508888
1094:15352787
1048:17367197
988:11027987
814:See also
791:Steroids
741:homologs
683:cofactor
655:aluminum
651:platinum
601:selenium
597:epoxides
593:oxidized
557:catalyst
509:include
507:oxidants
501:Reagents
435:peroxide
396:menthone
291:hydroxyl
238:while a
2519:A value
2387:6270215
2240:6314816
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777:lactone
675:enzymes
626:oxidant
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366:H or BF
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184:oxidant
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1481:S2CID
1013:(PDF)
726:liver
707:ester
695:NADPH
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551:>
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543:>
537:mCPBA
256:ester
170:or a
164:ester
91:mCPBA
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