Journal of the American Chemical Society

Thiapyran Derivatives. III. The Preparation, Properties and Reactions of▵ 2-Dihydrothiapyran 1, 1-Dioxide

EA Fehnel

Index: Fehnel Journal of the American Chemical Society, 1952 , vol. 74, p. 1569,1572

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Citation Number: 54

Abstract

The synthesis of A2-dihydrothiapyran 1, l-dioxide by an indirect route involving the Dieckmann cyclization of ethyl 7-(carbethoxymethy1mercapto)-butyrate is described. Rearrangement of the a, p-unsaturated sulfone to its p,?-unsaturated isomer, A3- dihydrothiapyran 1, l-dioxide, is observed to occur when A'-dihydrothiapyran l, l-dioxide is treated with triethylamine or dilute alkali. Addition of bromine to the a,@-unsaturated ...