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Synthesis 2009(7): 1105-1112  
DOI: 10.1055/s-0028-1088000
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-[(Arylmethylene)amino]cyclopropanecarbonitriles via a Two-Step Ring Transformation of 2-(Cyanomethyl)aziridines

Sven Mangelinckx, Matthias D’hooghe, Sietske Peeters, Norbert De Kimpe*
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@UGent.be;
Further Information

Publication History

Received 22 August 2008
Publication Date:
06 March 2009 (online)

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Abstract

Reaction of 2-(cyanomethyl)aziridines with N-bromosuccinimide in dichloromethane results in the formation of 3-[(arylmethylene)amino]-4-bromobutanenitriles in high yield. The latter β-amino-γ-bromobutanenitriles were converted into separable trans- and cis-2-[(arylmethylene)amino]cyclopropanecarbonitriles through a 1,3-cyclization by reaction with potassium tert-butoxide, thus culminating in a two-step ring transformation of 2-(cyano­methyl)aziridines into 2-[(arylmethylene)amino]cyclopropanecarbonitriles.

Key words

amino nitriles - cyclizations - 2-(cyanomethyl)aziridines - carbocycles - ring opening

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1

Postdoctoral Fellow of the Research Foundation - Flanders (FWO).