Tetrathiomolybdate mediated rearrangement of aziridinemethanol tosylates: a thia-aza-payne rearrangement

Sureshkumar, Devarajulu ; Koutha, Srinivasamurthy ; Ganesh, Venkataraman ; Chandrasekaran, Srinivasan (2010) Tetrathiomolybdate mediated rearrangement of aziridinemethanol tosylates: a thia-aza-payne rearrangement Journal of Organic Chemistry, 75 (16). pp. 5533-5541. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo100640w?ai=5...

Related URL: http://dx.doi.org/10.1021/jo100640w

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:7367
Deposited On:23 Oct 2010 09:02
Last Modified:01 Feb 2011 08:28

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