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Abstract Lewis‐acid‐catalyzed reactions of 2‐substituted cyclopropane 1,1‐dicarboxylates with thioketones are described. Highly substituted tetrahydrothiophenes with two adjacent quaternary carbon atoms were obtained in a stereospecific manner under mild conditions and in high yield when using AlCl 3 as Lewis acid. Moreover, an intramolecular approach was successfully implemented to gain access to sulfur‐bridged n .2.1 bicyclic ring systems. Conversion of selenoketones, the heavier analogues, under similar conditions resulted in the formation of various tetrahydroselenophenes.
Augustin et al. (Tue,) studied this question.