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Trends in Heterocyclic Chemistry   Volumes    Volume 8 
Competitive 1,3-cycloaddition of benzonitrile oxides to carbon-carbon and carbon-nitrogen multiple bonds
Enzo Cadoni, Gioanna Gelli, Paolo Beltrame
Pages: 85 - 94
Number of pages: 10
Trends in Heterocyclic Chemistry
Volume 8 

Copyright © 2002 Research Trends. All rights reserved


This review covers the 1, 3-cycloaddition of benzonitrile oxides to dipolarophiles that contain both C=N (or C≡N) and C=C (or C≡C) bonds and in several cases it is the unsaturated carbon-nitrogen bond that is the preferred site of competitive attack. There are cases when there is no attack at the C=C bond, while in other cases attack does occur but it is accompanied by structural modifications, like the elimination of small molecules (NH3, H2, amines), closure to make a further ring or the opening of an existing one and, sometimes, further reaction of the primary product.

A small substituent effect was found when variously substituted benzonitrile oxides were considered. Thus, the choice of the aryl nitrile oxide is usually not critical for either the reaction products or the reaction rate.

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