Sureshkumar, Devarajulu ; Koutha, Srinivasamurthy ; Chandrasekaran, Srinivasan (2007) A new selena-aza-payne-type rearrangement of aziridinylmethyl tosylates mediated by tetraselenotungstate European Journal of Organic Chemistry, 2007 (27). pp. 4543-4551. ISSN 1434-193X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...
Related URL: http://dx.doi.org/10.1002/ejoc.200700357
Abstract
Tetraselenotungstate 1 reacts with simple (N-tosylaziridinyl)methyl tosylate derivatives to give allylamine derivatives as the only products by an unprecedented selena-aza-Payne-type rearrangement. When the methodology is extended to disubstituted (N-tosylaziridinyl)methyl tosylates, regio- and stereospecific ring-opening of the aziridines occurs to afford allylamine derivatives as the major products and cyclic five-membered diselenides as the minor products in good yields under mild reaction conditions without using any Lewis acid or base.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
| Keywords: | Aziridines; Aza-payne Rearrangement; Selenium Nucleophiles; Allylamines; Cyclic Diselenides |
| ID Code: | 7324 |
| Deposited On: | 25 Oct 2010 11:49 |
| Last Modified: | 01 Feb 2011 09:26 |
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