Mechanistic aspects of reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution

Abstract

Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate-determining step in quarternization reactions of triphenylphosphine with electron-deficient alkenes in acetic acid solution. This conclusion is based on the third-order rate equation, the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. Copyright © 2013 John Wiley & Sons, Ltd