α,β-Epoxy sulfones. The Darzens condensation with α-halosulfones
- 1 August 1969
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 47 (15) , 2875-2881
- https://doi.org/10.1139/v69-477
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.Keywords
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