Reactivity of Phenyl Vinyl Selenide with Nucleophiles and Bases

Abstract

Four possible reactions of phenyl vinyl selenide (CH2CHSePh) have been discovered on treatment with nucleophiles or bases: SeC cleavage, addition, metalation, elimination. The reaction pathway is very sensitive to solvent and reaction conditions. The species (1), (2), and/or (3) may be formed initially with nBuLi, and (3) and/or (4) (+acetylene) with LiN(iPr)2.