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Hypervalent iodine-mediated aziridination of alkenes: Mechanistic insights and requirements for catalysis

Richardson, Robert David, Desaize, Magalie and Wirth, Thomas 2007. Hypervalent iodine-mediated aziridination of alkenes: Mechanistic insights and requirements for catalysis. Chemistry - A European Journal 13 (23) , pp. 6745-6754. 10.1002/chem.200700306

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Abstract

By detailed study of the possible side reactions in the previously reported aziridination of alkenes with N-aminoheterocycles mediated by hypervalent iodine reagents, the requirements to make this reaction catalytic in iodoarene have been determined. The reaction requires an oxidant that will oxidise iodoarenes but that does not oxidise alkenes, but it is possible that no such oxidant actually exists! A method in which the hypervalent iodine reagent can be recycled without the need for reisolation is possible. Further study into the mechanism of this reaction gives tentative evidence that the reaction proceeds through formation of an aminoiodane that reacts directly with the alkene, contrary to previous literature reports in which an acetoxyamine intermediate is suggested. The temperature effect of this reaction is remarkable.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: aziridines; hypervalent compounds; iodine; reaction mechanism; oxidation
Publisher: Wiley-Blackwell
ISSN: 1521-3765
Last Modified: 04 Jun 2017 02:08
URI: http://orca-mwe.cf.ac.uk/id/eprint/9772

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