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Cycloadditions of Nitrile Oxides to α,β-Unsaturated Aldehydes. Frontier Orbital Interactions and Secondary Orbital Interactions at Work in Determining Regiochemistry

✍ Scribed by Lucio Toma; Paolo Quadrelli; Giancarlo Perrini; Remo Gandolfi; Cristiana Di Valentin; Antonino Corsaro; Pierluigi Caramella

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 195 KB
Volume: 56
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(00)00356-2

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✦ Synopsis

AbstractÐThe regiochemistry of the cycloadditions of nitrile oxides to crotonaldehyde and cinnamaldehyde has been determined and is dictated by frontier orbital interactions and secondary orbital interactions as well. In cycloadditions to a,b-unsaturated compounds the directive effect of the frontier orbital interactions can be diverted by steric drifts and secondary orbital interactions.

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