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DOI: 10.1055/sos-SD-037-00188

Aggarwal, V. K.; Crimmin, M.; Riches, S.Science of Synthesis, (200837323.

In 1960, Wittig reported the reaction of methylene(triphenyl)arsorane (triphenylarsonium methylide, 6) with benzophenone to yield a 1:1 mixture of triphenylarsine oxide and (1-phenylvinyl)benzene (9), along with a 1:1 mixture of triphenylarsine and diphenylacetaldehyde (8) (Scheme 4).[‌22‌] Aldehyde 8 is believed to be derived from an intermediate epoxide 7 via path a, whereas alkene 9 is proposed to form via path b. It has since been shown that arsonium ylides react with carbonyl groups to give a mixture of alkenation and epoxidation products that is dependent upon the stability of the arsonium ylides,[‌23‌] the structure of the carbonyl electrophile, and in some cases the reaction conditions.[‌24‌,‌25‌] In general, nonstabilized arsonium ylides give higher yields of epoxides than alkenes, whereas more stabilized ylides tend toward alkenation (see Scheme 6, Section

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