Cleavage of 1,3-Dithianes via Acid-Catalyzed Hydrolysis of the Corresponding 1,3-Dithianemonooxides

Abstract

The hydrolysis of 1,3-dithianes to their parent carbonyl compounds via their corresponding monosulfoxides was systematically investigated. The oxidation of the 1,3-dithianes was carried out in high yields using tert-butyl hydroperoxide. Acid-catalyzed hydrolysis of the monosulfoxides to the carbonyl compounds was then performed in excellent yields. The cleavage reactions were monitored by gas chromatography and kinetics were investigated on substrates varying in electron density and steric requirements. Neither effect prevented high overall yields in the cleavage reaction.

Key words

1,3-dithianes - dithioacetals - 1,3-dithiane-1-oxides - cleavage - dethioacetalization

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