Helvetica Chimica Acta

Regioselektive 1, 3??dipolare Cycloadditionen von Thiocarbonyl??yliden mit 1, 3??Thiazol??5 (4H)??thionen

G Mlostoń, A Linden, H Heimgartner

Index: Mloston, Grzegorz; Linden, Anthony; Heimgartner, Heinz Helvetica Chimica Acta, 1991 , vol. 74, # 7 p. 1386 - 1398

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Abstract

The thiocarbonyl ylides 13 and 1, 3-thiazol-5 (4H)-thiones 1 undergo a smooth reaction to yield spirocyclic 1, 3-dithioIanes 14-16 (Schemes 4 4). The 1, 3-dipolar cycloadditions occur in a regioselective manner, but the orientation of the thiobenzophenone-S-methylide (13b) differs from that of the cycloalkane thione-S-methylides 13a and 13c. Whereas the 1, 3- cycloadduct with 13b is formed in accordance with frontier-orbital considerations, the ...