Synlett 2007(18): 2912-2918  
DOI: 10.1055/s-2007-990960
LETTER
© Georg Thieme Verlag Stuttgart · New York

Facile Generation and Synthetic Utility of Nitrogen-Centered Aziridinyl Radicals

Xiaoyang Yang, Andrei K. Yudin*
Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada
Fax: +1(416)9467676; e-Mail: ayudin@chem.utoronto.ca;
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Publication History

Received 25 May 2007
Publication Date:
19 October 2007 (online)

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Abstract

Nitrogen-centered aziridinyl radicals can be generated through homolysis of N-haloaziridines, which can be easily produced upon treatment of NH aziridines with N-bromo- or N-iodo­succinimide. This methodology allows synthesis of a variety of β-haloaziridines in moderate to good yields. Further transformation into piperazine scaffolds can be achieved via nucleophilic substitution at the β-position and aziridine ring opening initiated by oxalyl chloride.

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