Ring-Opening Reaction of Methylenecyclopropanes Derived from Methylenecyclopropyl Aldehydes through Cope Rearrangement

[摘要]：Tandem Wittig reaction/Cope rearrangement of methylenecyclopropyl aldehydes 1 with cinnamyltriphenylphosphonium bromide afforded a convenient method for the synthesis of cyclopentene derivatives 2 in moderate yields in a one-pot manner. Dialkyl 2-[(2-methylenecyclopropyl)methylene]malonates 3 derived from methylenecyclopropyl aldehydes 1 could produce two kinds of cyclopentene derivatives, 4 and 5, in good total yields through a thermally induced Cope rearrangement upon heating at 100 degrees C. Plausible reaction mechanisms are discussed on the basis of previous reports and on control experiments.

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