Photochemistry of 2-phenyl-1, 2-dihydronaphthalene. A competition between a singlet state di-. pi.-methane rearrangement and a ring-opening reaction

JJM Lamberts, WH Laarhoven

Index: Lamberts, Joseph J.M.; Laarhoven, Wim H. Journal of the American Chemical Society, 1984 , vol. 106, # 6 p. 1736 - 1739

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Citation Number: 7

Abstract

Abstract: Irradiation of 2-phenyl-l, 2-dihydronaphthalene (4) at 300 nm in hexane leads to three primary photoproducts: endo-and exo-6-phenylbenzobicyclo [3.1. O] hex-2-ene (endo- 5 and exc-5) and 7, 12-dihydrodibenzo [a, dlcyclooctatetraene (6). Irradiation of labeled 4 (4- 3, 4-d2) showed that 5 arises via a di-n-methane rearrangement as well as via electrocyclic ring opening, single bond rotation, and photocycloaddition. The di-n-methane ...