Abstract
A range of substituted 3,3,4,4-tetracyano-6,8-dithiabicyclo[3.2.1]octanes, viz. compounds 5dg, 5j–m, and 5o–u, have been synthesized from the corresponding allyl dithiocarboxylates by a cation radical cycloaddition reaction, using tetracyanoethylene 2 in acetonitrile. The reaction scope has been studied and the mechanism proposed on the basis of the dithioester's chemical behaviour in respect to oxidizing agents, mass-spectrometry data, the substituent effect analysis as well as by quantum chemical calculations by the MINDO/3 method in UHF approach.
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