Kinetics of retro-cyanoethylation of phosphonium salts and the question of phosphole aromaticity

Abstract
Phospholium ion (1) is cleaved by sodium methoxide into 1,2,5-triphenylphosphole and acrylonitrile at a rate substantially greater than that observed for comparable phosphonium ions, a finding which is consistent with significant delocalization of the lone electron pair on phosphorus in phospholes.

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