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Synthesis 2006(13): 2260-2264
DOI: 10.1055/s-2006-942421
DOI: 10.1055/s-2006-942421
PAPER
© Georg Thieme Verlag Stuttgart · New York
Reaction of Electrophilic Allyl Halides with Amines: A Reinvestigation
Weitere Informationen
Received
4 January 2006
Publikationsdatum:
12. Juni 2006 (online)
Publikationsverlauf
Publikationsdatum:
12. Juni 2006 (online)
![](https://www.thieme-connect.de/media/synthesis/200613/lookinside/thumbnails/10.1055-s-2006-942421-1.jpg)
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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