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

John Gullick, Sophia Taylor, Paul McMorn, Donald Bethell, Philip C. Bulman Page, Frederick E. Hancock, Frank King, Graham Hutchings

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22 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)85-89
Number of pages5
JournalJournal of Molecular Catalysis A: Chemical
Volume180
Issue number1-2
DOIs
Publication statusPublished - 2002

Keywords

  • aziridination
  • OLEFINS
  • nitrene donors
  • chloramine-T
  • HETEROGENEOUS AZIRIDINATION

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