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.

GRAPHICAL ABSTRACT

Keywords:

• decarboxylation
• Knoevenagel-type condensation
• arylsulfonylacetic acid derivatives
• sulfonium betaines
• reactivity trends

Additional information

Funding

This work was supported by the National Institute of Health [1R15GM085936], National Science Foundation [CHE 0957482], and the Camille and Henry Dreyfus Foundation [TH-06-008].