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Anomalous Epoxide Formation Upon Wittig Olefination With 1-Iodoethyl Triphenylphosphonium Ylide

Hirokazu Arimoto, Michael D. Kaufman, Kaoru Kobayashi, Yuping Qiu, Amos B. Smith

Abstract

All articles of this category Reaction of iodo Wittig ylide 1 with aldehyde 2 affords moderate yields of cis epoxides 6a and 7a , in addition to the expected olefin 3 . A mechanism is proposed to account for both the high Z selectivity and the modest yield of olefin observed with this reagent. Z -olefination - iodo Wittig ylids - α , β -epoxy phosphonium salts

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Available abstract

Key concepts: Wittig reaction, Ylide, Chemistry, Olefin fiber, Epoxide, Aldehyde, Yield (engineering), Reagent