trans 1-Chloro- and 2-chloro-5-phenylpent-1-enes undergo selective intramolecular photocycloaddition of the ethene to the 1,3-positions of the phenyl ring, and the cyclopropane ring formation in the adduct is controlled by the chlorine substituent to give specific access to either the angular or linear triquinane carbon skeleton respectively.
K. Cosstick and A. Gilbert, J. Chem. Soc., Perkin Trans. 1, 1989, 1541 DOI: 10.1039/P19890001541
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