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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
Author(s) -
Sundermeyer Wolfgang,
Walch Andreas
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961290209
Subject(s) - chemistry , silylation , nuclear magnetic resonance spectroscopy , methylene , alkyl , knoevenagel condensation , carbon 13 nmr , spectroscopy , medicinal chemistry , organic chemistry , stereochemistry , catalysis , physics , quantum mechanics
Sulfoxonium ylides 3a‐h were synthesized by silylation 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 nonafluorobutanesulfonates. The structure and constitution of the ylides were established with 1 H‐NMR, 13 C‐NMR, 29 Si‐NMR spectroscopy, mass spectrometry, and elemental analysis. On the route to the sulfoxonium 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 1 H‐NMR and 13 C‐NMR spectroscopy and compared with the results of the ylides.