Intramolecular-activation evidence for the unexpected Beckmann fragmentation of C(1)-substituted-7-bromonorbornane-2-ones

The competitive pathway timing for the previously described unexpected bromo-assisted Beckmann fragmentation of 7- anti-bromo-3,3-dimethyl-2-oxonorbornane-1-carboxamide has been investigated. It is concluded that this unusual process is activated by a synergic effect exerted by both the C(7)- anti-b...

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Bibliographic Details
Published in:Tetrahedron 2004-10, Vol.60 (42), p.9447-9451
Main Authors: García Martínez, Antonio, Teso Vilar, Enrique, García Fraile, Amelia, de la Moya Cerero, Santiago, Lora Maroto, Beatriz
Format: Article
Language:English
Subjects:
Bicycles
Bridgehead compounds
Cleavage reactions
Substituent effects
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Summary:The competitive pathway timing for the previously described unexpected bromo-assisted Beckmann fragmentation of 7- anti-bromo-3,3-dimethyl-2-oxonorbornane-1-carboxamide has been investigated. It is concluded that this unusual process is activated by a synergic effect exerted by both the C(7)- anti-bromo and C(1)-aminocarbonyl groups. The effect consists in a specific intramolecular activation of the bromo-assistance by the bridgehead aminocarbonyl group. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.08.002