Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S, N-acetals and thioisomünchnones

…, CB de Koning, CW van der Westhuyzen…

Index: Michael, Joseph P.; De Koning, Charles B.; Van der Westhuyzen, Christiaan W.; Fernandes, Manuel A. Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 17 p. 2055 - 2062

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Citation Number: 21

Abstract

Reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction. However, with 3-substituted piperidine-2-thiones, sulfur was retained in the products, and a range of bicyclic heterocycles, including bicyclic ketene S, N-acetals (2-alkylidene-1, 3-thiazolidin-4-ones) and stable thioisomünchnones, was isolated. A novel dimeric ketene S, N-acetal was ...