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Synthesis, Thermal and Photochemical Reactions of New Mesoionic 1,3,2-Oxathiazolones
Gotthardt, Hans,Reiter, Friedemann,Kromer, Claudia
, p. 1025 - 1034 (2007/10/02)
The synthesis and spectroscopic data of the new mesoionic 1,3,2-oxathiazolones 3b, c, e are described.As cyclic thiocarbonyl imine, 3e reacts with dimethyl acetylenedicarboxylate at 80 deg C with evolution of carbon dioxide to produce the 5-arylisothiazole derivative 6e (80percent).On the other hand, the visible light-induced fragmentation of 3e leads to a nitrile sulfide intermediate of type 10 which suffers unimolecular decay with formation of sulfur and the arylnitrile 11e or which can be partially trapped with dimethyl acethylenedicarboxylate to form the iosmeric 3-arylisothiazole derivative 13e (29-21percent).The analogous photochemical decay of 3c in the presence of dimethyl acetylenedicarboxylate proceeds with formation of the isothiazole derivative 13c besides sulfur and the nitrile 11c, whereas the nitrile sulfide 10b - photochemically generated from 3b - does not more react with formation of an isothiazole derivative.
