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Original Articles

REARRANGEMENT IN THE ACETYLENIC NUCLEOPHILIC SUBSTITUTION WITH THE O-ALKYL CARBONODITHIOATE ANIONS

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Pages 81-89 | Received 08 Jun 1999, Published online: 04 Oct 2006
 

Abstract

(Alkylthio)chloroacetylenes react with potassium O-alkyl carbonodithioates under mild conditions (25–30°C, DMSO) to form an approximately equimolar mixture of O-alkyl-S-[2-(alkylthio)ethynyl] carbonodithioates and S-alkyl-S-[2-(alkylthio)ethynyl] carbonodithioates in a total yield of up to 65%. The rearrangement is proved to occur in an anionic intermediate, probably, of the thiete structure.

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