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wharton reaction wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 mechanism and scope 2 applications 3 references 4 see also toggle the table of contents wharton reaction 6 languages deutsch español فارسی português українська 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction the wharton olefin synthesis or the wharton reaction is a chemical reaction that involves the reduction of α β epoxy ketones using hydrazine to give allylic alcohols 1 2 3 this reaction introduced in 1961 by p s wharton is an extension of the wolff kishner reduction the general features of this synthesis are 1 the epoxidation of α β unsaturated ketones is achieved usually in basic conditions using hydrogen peroxide solution in high yield 2 the epoxy ketone is treated with 2 3 equivalents of a hydrazine hydrate in presence of substoichiometric amounts of acetic acid this reaction occurs rapidly at room temperature with the evolution of nitrogen and the formation of an allylic alcohol 1 it can be used to synthesize carenol compounds wharton s initial procedure has been improved 4 the wharton reaction mechanism and scope edit the mechanism of the wharton reaction begins with reaction of the ketone 1 with hydrazine to form a hydrazone 2 rearrangement of the hydrazone gives intermediate 3 which can decompose giving off nitrogen gas forming the desired product 4 the final decomposition can proceed by an ionic or a radical pathway depending on reaction temperature solvent used and structure of intermediate 3 5 the mechanism of the wharton reaction the wharton olefin synthesis allows the transformation of an α β unsaturated ketone into an allylic alcohol the epoxide starting material can be generated by a number of methods with the most common being reaction of the corresponding alkene with hydrogen peroxide or m chloroperoxybenzoic acid the wharton reaction also commonly suffers from reduction of the allylic alcohol product down to the aliphatic alcohol this is thought to be due to the oxidation of hydrazine to diimide under the conditions employed in the reaction 6 the classical wharton olefin synthesis has two limitations the classical wharton olefin synthesis conditions are not free from the presence of water so reactants undergoing the wharton olefin synthesis should not be sensitive to water for acyclic α β unsaturated ketones the wharton olefin synthesis does not show any selectivity for a specific configuration of the newly synthesized double bond in terms of e or z stereoisomers applications edit the methodology has been implemented in synthesis of complex molecules the total synthesis of the anticancer natural product osw 1 provides a practical application of the wharton olefin synthesis an α β epoxyketone reacts with hydrazine hydrate to yield an allylic alcohol 7 in the synthesis of warburganal a bioactive natural product the α β epoxyketone is formed from a cyclic α β unsaturated ketone and in a separate step reacts under the classical wharton olefin synthesis conditions to yield an allylic diol 8 references edit 1 2 wharton p s bohlen d h 1961 communications hydrazine reduction of α β epoxy ketones to allylic alcohols j org chem 26 9 3615 doi 10 1021 jo01067a117 wharton p s 1961 communications stereospecific synthesis of 6 methyl trans 5 cyclodecenone j org chem 26 11 4781 4782 doi 10 1021 jo01069a609 chamberlin a r sall d j 1991 reduction of ketones to alkenes compr org synth 8 927 929 doi 10 1016 b978 0 08 052349 1 00251 1 isbn 978 0 08 052349 1 cite journal cs1 maint periodical has isbn link dupuy c luche j l 1989 new developments of the wharton transposition tetrahedron 45 11 3437 doi 10 1016 s0040 4020 01 81022 x stork g a williard p g 1977 five and six membered ring formation from olefinic α β epoxy ketones and hydrazine j am chem soc 99 21 7067 doi 10 1021 ja00463a053 hutchins r o 1991 comp org synth oxford pergamon pp 341 342 yu w jin z 2002 total synthesis of the anticancer natural product osw 1 journal of the american chemical society 124 23 6576 6583 doi 10 1021 ja012119t pmid 12047177 cite journal cs1 maint multiple names authors list link barrero a f cortes m manzaneda e a cabrera e chahboun r lara m rivas a 1999 synthesis of 11 12 epoxydrim 8 12 en 11 ol 11 12 diacetoxydrimane and warburganal from sclareol j nat prod 62 11 1488 1491 citeseerx 10 1 1 379 6604 doi 10 1021 np990140q pmid 10579858 cite journal cite uses deprecated parameter citeseerx help cs1 maint multiple names authors list link see also edit eschenmoser fragmentation grob fragmentation wolff kishner reduction retrieved from https en wikipedia org w index php title wharton_reaction oldid 1282473783 categories organic redox reactions name reactions hidden categories articles with short description short description matches wikidata cs1 maint periodical has isbn cs1 maint multiple names authors list cs1 errors deprecated parameters this page was last edited on 26 march 2025 at 16 51 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia 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