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A New Selena‐Aza‐Payne‐Type Rearrangement of Aziridinylmethyl Tosylates Mediated by Tetraselenotungstate
Author(s) -
Sureshkumar Devarajulu,
Koutha Srinivasamurthy,
Chandrasekaran Srinivasan
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700357
Subject(s) - allylamine , chemistry , stereospecificity , lewis acids and bases , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis , polymer , polyelectrolyte
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)