Mechanism of photochemical meta-cycloaddition of alkenes to the benzene ring: a novel type of molecular interaction
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 9,p. 607-609
- https://doi.org/10.1039/c39850000607
Abstract
The regioselectivity of photochemical meta-cycloaddition of alkenes to alkylbenzenes changes progressively from 2,6- to 3,5- with increasing size of the alkyl group(s) while retaining endostereospecificity: this finding implies a novel type of weak but orienting intermolecular bonding interaction (intermolecular hyperconjugation) between S1 benzene and α-hydrogens on the alkene which can predominate over steric effects of bulky alkyl groups.Keywords
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