Reactions of 1,3-dithiolane 1,3-dioxides with nucleophiles

Abstract

Reaction of benzenethiol with the 1,3-dithiolane 1,3-dioxides 3a–f gave the 1,4-dithiane 1-oxides 4–5, the αβ-unsaturated sulfoxides 6–9, the ring-opening products 10–11 and various reduction products. Addition of benzenethiol, malononitrile, diethyl malonate or 2-mercapto-4,5-dihydrothiazole to the double bonds of the 2-alkenyl-1,3-dithiolane 1,3-dioxides 3g–h was performed with methylmagnesium chloride in methanol. Addition of methanol or an allyl group to the dioxide 3h occurred regioselectively to give the 1,3-dithiolane 1-oxide 19 or the 1,3-dithiolane 20.