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

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Abstract
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.

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