The Photochemistry of 2-Cyano-1,4-dihydro-1,4-ethenoanthracene

Abstract
The direct photolysis of 2-cyano-1,4-dihydro-1,4-ethenoanthracene (5) yields 8-cyanocycloocta[b]-naphthalene (8, Φ = 0.02) and 1- and 6-cyanonaphtho[2,3-c]tricyclo-[3.3.0.02,8]octa-3,6-diene (6, Φ = 0.30 and 7, Φ = 0.04). The benzophenone sensitized irradiation of 5 yields 6 (Φ = 0.40) and 7 (Φ = 0.04) only. Deuterium labeling studies reveal that 8 derives from an initial 2π + 2π cycloaddition reaction which proceeds with bonding between the vinyl and vinylcyano bridges.

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