Generation, trapping, and adduct rearrangement of 3-phenylselenoalk-1-enylidene carbenes: a novel direct route to 1-hetero-substituted 1-vinylcyclopropanes

Abstract

3-Phenylselenoalk-1-enylidene carbenes, generated in situ by base-induced Horner–Wadsworth–Emmons condensation of α-phenylseleno carbonyl compounds and diethyl diazomethylphosphonate, may be efficiently trapped to give alkylidene-cyclopropane adducts which undergo either [1,3]allyl selenide rearrangement or oxidative selenoxide[2,3]sigmatropic rearrangement to produce 1-heterosubstituted 1-vinylcyclopropanes.