Tetrathiomolybdate Mediated Rearrangement of Aziridinemethanol Tosylates: A Thia-Aza-Payne Rearrangement

Aziridinemethanol sulfonate esters react with tetrathiomolybdate 1 to give thiirane derivatives as the major product and cyclic disulfides as minor product under mild reaction conditions via an unprecedented thia-aza-Payne-type rearrangement. Interestingly, when the reaction of 1 was carried out with 2-aziridino-cyclohexanol derivatives it resulted in the formation of thia-bicyclo[3.1.1]heptane or dithia-bicyclo[3.2.1]octane derivatives.

在温和反应条件下，氮丙啶甲醇磺酸酯类化合物与四硫代钼酸盐1发生反应，经由前所未有的硫-氮杂Payne型重排路径，以环硫乙烷衍生物为主要产物、环二硫化物为次要产物。值得注意的是，当四硫代钼酸盐1与2-氮丙啶基环己醇类化合物进行反应时，可生成硫杂双环[3.1.1]庚烷或二硫杂双环[3.2.1]辛烷衍生物。