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Synthesis 2006(13): 2260-2264  
DOI: 10.1055/s-2006-942421
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reaction of Electrophilic Allyl Halides with Amines: A Reinvestigation

Sven Mangelinckxa, Dirk Courtheyna, Roland Verhéa, Veronique Van Speybroeckb, Michel Waroquierb, Norbert De Kimpe*a
a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, 9000 Ghent, Belgium
b Laboratory of Theoretical Physics, Ghent University, Proeftuinstraat 86, 9000 Ghent, Belgium
Fax: +32(9)2646243; e-Mail: norbert.dekimpe@UGent.be;
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Publication History

Received 4 January 2006
Publication Date:
12 June 2006 (online)

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Abstract

The Michael-induced ring closure (MIRC) of amines with 2-bromoalkylidenemalonates has been reinvestigated and the reaction products with primary amines have been identified as (2-iminoethyl)malonates and not 2-aminoalkylidenemalonates as previously reported. The (2-iminoethyl)malonates are formed by ring opening of the intermediate unstable 2-aminocyclopropane-1,1-dicarboxylates (β-ACCs) and were characterized spectroscopically and via chemical transformation.

Key words

Michael additions - ring closure - cyclopropanes - ring opening - imines