On the synthesis of sulfoxonium ylides: New aspects of the chemistry of 1,3-dithietane 1,1,3,3-tetraoxide and 1,3,5-trithiane 1,1,3,3,5,5-hexaoxide

Article abstract of DOI:10.1002/cber.19961290209

Sulfoxonium ylides 3a-h were synthesized by silyiation of the cyclic methylene disulfones 1,3-dithietane 1,1,3,3-tetraoxide (1) and 1,3,5-trithiane 1,1,3,3,5,5-hexaoxide (4) with the silylating agents silyl nonailuorobutanesulfonates. The structure and constitution of the ylides were established with ¹H-NMR, ¹³C-NMR, ²⁹Si-NMR spectroscopy, mass spectrometry, and elemental analysis. On the route to the sulfoxo-niurn ylides a new class of unsaturated disulfenes 7, 8, 12, 13 of 1 and 4 were synthesized via Knoevenagel and substitution reactions. Dianions of newly formed alkyl disulfenes 16a, b, e, f, and the trianion 17 were prepared and characterized by ¹H-NMR and ¹³C-NMR spectroscopy and compared with the results of the yiides. VCH Verlagsgeseullschaft mbH 1996.