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Synlett 2015; 26(10): 1371-1374
DOI: 10.1055/s-0034-1380521
letter
© Georg Thieme Verlag Stuttgart · New York

Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines

Frances H. Bayliffe
a   Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK   Email: m.shipman@warwick.ac.uk
,
Alan Steven
b   AstraZeneca Pharmaceutical Development, Charter Way, Macclesfield SK10 2NA, Cheshire, UK
,
Kaori Ando
c   Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan
,
Michael Shipman*
a   Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK   Email: m.shipman@warwick.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 26 January 2015

Accepted after revision: 12 March 2015

Publication Date:
01 April 2015 (online)

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Abstract

The effect of the halogen on the rate of sodium amide induced cyclization of 2-haloprop-2-enylamines to methyleneaziridines is studied. Using DFT calculations and competition experiments, it is shown to proceed faster using iodide-based substrates. A practical route to 1-aryl-2-methyleneaziridines is devised based on these observations and their further rearrangement to cyclopropanimines explored.

Key words

aziridines - cyclization - aminocyclopropanes - DFT calculations - vinylic SN2

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380521.
  • Supporting Information
 

  • References and Notes

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