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

…, S Koutha, V Ganesh, S Chandrasekaran

Index: Sureshkumar, Devarajulu; Koutha, Srinivasamurthy; Ganesh, Venkataraman; Chandrasekaran, Srinivasan Journal of Organic Chemistry, 2010 , vol. 75, # 16 p. 5533 - 5541

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Citation Number: 2

Abstract

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.