α,β-Epoxy sulfones. The Darzens condensation with α-halosulfones

Abstract

Darzens type condensation of chloromethyl p-tolyl sulfone with benzaldehyde, acetaldehyde, acetone, benzophenone, and cyclohexanone, with potassium tert-butoxide as base, gave good to excellent yields of the corresponding α,β-epoxy sulfones (1). The condensation of α-chloroethyl p-tolyl sulfone and bromomethyl p-tolyl sulfone with benzaldehyde also gave excellent yields. With the aldehydes only the trans-epoxides were formed, which is shown by nuclear magnetic resonance spectroscopy. The mechanism and stereochemistry are discussed.