Novel 2-alkyl-1-benzotellurepines (11) and 2-alkyl-1-benzoselenepines (12) were obtained by sodium borohydride reduction of di[o-(1-buten-3-ynyl)phenyl] ditellurides (8) and diselenides (9), together with 2-alkylidene-2H-tellurachromenes (13) and 2-alkylidene-2H-selenachromenes (14), respectively, via the phenyltellurol and phenylselenol intermediates (10). The dimers (8, 9) were readily prepared from the 4-alkyl-1-(o-bromophenyl)-1-buten-3-ynes (7) by successive treatment with tert-butyllithium, tellurium or selenium powder, and potassium ferricyanide in one pot. The 2-alkyl-1-benzothiepines (16) were obtained directly from the enynes (7) by successive treatment with tert-butyllithium, sulfur powder, and ethanol in one pot. To examine the chemical behavior of the novel tellurepine ring, several reactions of 2-tert-butyetellurepine (11c) weree carried out.
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Sashida et al. (1995) studied this question.