Aziridination of styrene: comparison of N-(p-tolylsulfonyl)imino phenyliodinane and chloramine-T as nitrene donors

Gullick, John, Taylor, Sophia, McMorn, Paul, Bethell, Donald, Bulman Page, Philip C., Hancock, Frederick E., King, Frank and Hutchings, Graham (2002) Aziridination of styrene: comparison of N-(p-tolylsulfonyl)imino phenyliodinane and chloramine-T as nitrene donors. Journal of Molecular Catalysis A: Chemical, 180 (1-2). pp. 85-89. ISSN 1381-1169

Full text not available from this repository. (Request a copy)

Abstract

Chloramine-T and [N-(p-tolylsulfonyl)imino]phenyliodinane (PhI=NTs) are contrasted as nitrene donors for the aziridination of styrene using copper(II) triflate, and copper-exchanged zeolite Y (CuHY) as catalysts. For both catalysts, PhI=NTs is found to give significantly higher yields of the aziridine both in the presence and absence of a chiral bis(oxazoline) modifier. In addition, chloramine-T is found to induce leaching of most of the Cu from CuHY, and with this nitrene donor CuHY does not function as a heterogeneous catalyst. In contrast, PhI=NTs causes negligible leaching of Cu from CuHY and, consequently, for the heterogeneous CuHY catalyst, PhI=NTs is the preferred nitrene donor. With chloramine-T, the beneficial effects observed on addition of copper powder are shown to be due to the copper powder acting as a reservoir for Cu2+ in solution, since Cu2+ in solution is rapidly deactivated by toluenesulfonamide, a degradation product of the nitrene donor. (C) 2002 Elsevier Science B.V. All rights reserved.

Item Type: Article
Uncontrolled Keywords: aziridination,olefins,nitrene donors,chloramine-t,heterogeneous aziridination
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 10:48
Last Modified: 21 Apr 2020 20:46
URI: https://ueaeprints.uea.ac.uk/id/eprint/32834
DOI: 10.1016/S1381-1169(01)00419-8

Actions (login required)

View Item View Item