Phenylsulfonylacetic acid: condensations onto aryl aldehydes

Abstract

A study involving scope in the condensation reaction of phenylsulfonylacetic acid with a series of carbonyl derivatives has been conducted. Reactivity trends favor formation of the corresponding vinyl sulfones when working with aryl aldehydes. Electron-deficient aryl aldehydes outperform electron-rich aryl aldehydes. Negligible differences were noted when using electron-rich and electron-deficient arylsulfonylacetic acid derivatives. Post-run analyses of the reaction mixture reveal formation of a minor product which resulted from methylidene transfer onto the carbonyl derivative. Support of a Knoevenagel-type condensation followed by decarboxylation is provided.