Reaction of Electrophilic Allyl Halides with Amines: A Reinvestigation

Sven Mangelinckx; Dirk Courtheyn; Roland Verhé; Veronique Van Speybroeck; Michel Waroquier; Norbert De Kimpe

doi:10.1055/s-2006-942421

PAPER

Reaction of Electrophilic Allyl Halides with Amines: A Reinvestigation

Sven Mangelinckx^a, Dirk Courtheyn^a, Roland Verhé^a, Veronique Van Speybroeck^b, Michel Waroquier^b, 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;

Abstract

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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

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References

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