trans-1,2-Dicloroethene undergoes 2,4-photocycloaddition to benzonitrile to yield 4-cyano-6-exo-7-endo-diclorotricyclo [3.3.0.02,8]oct-3-ene (3) as the major product, the structure of which has been determined by X-ray crystallography; steric and radical stabilization factors of the addend substituents are considered to direct the reaction to this specific mode of meta attack.
M. G. B. Drew, A. Gilbert, P. Heath, A. J. Mitchell and P. W. Rodwell, J. Chem. Soc., Chem. Commun., 1983, 750 DOI: 10.1039/C39830000750
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