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The 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 α,β-unsaturated compounds the directive effect of the frontier orbital interactions can be diverted by steric drifts and secondary orbital interactions.
The regiochemistry of the cycloadditions of nitrile oxides to α,β-unsaturated amides is determined by frontier orbital interactions and by a regiochemical drift due to steric effects. Cycloadditions to α,β-unsaturated lactames afford mainly 4-carboxamido-isoxazolines with high regioselectivity. In cycloadditions to acyclic α,β-unsaturated amides the regioselectivity relaxes and finally reverses...
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