Journal of heterocyclic chemistry

Synthesis of small??medium ring thioanhydrides

MJ Kates, JH Schauble

Index: Kates, Michael J.; Schauble, J. Herman Journal of Heterocyclic Chemistry, 1995 , vol. 32, # 3 p. 971 - 978

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Citation Number: 10

Abstract

Abstract Reaction of five-membered ring anhydrides with sodium sulfide has previously been employed for synthesis of the corresponding thioanhydrides in low yields. Re- examination of the stoichiometry reveals reaction of cyclic anhydride with sodium sulfide (2: 1 respectively), affords the thioanhydride accompanied by the corresponding dicarboxylate in a 1: 1 molar ratio. The mechanistic pathway for this reaction has also been elucidated. ...