Photochemical transformations of small ring heterocyclic compounds. LXII. Competitive keto-enolate photochemistry in the 3-phenylcoumaran-2-one system

A Padwa, D Dehm, T Oine, GA Lee

Index: Padwa,A. et al. Journal of the American Chemical Society, 1975 , vol. 97, # 7 p. 1837 - 1845

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Citation Number: 50

Abstract

Abstract: The photochemistry of 3-phenylisocouniaranone (1) is markedly influenced by the tautomeric composition of the lactone in solution. Decarbonylation results from excitation of the keto tautomer using 2537-A light. The transient o-quinone methide formed rapidly reacts with methanol to give o-hydroxybenzhydryl methyl ether (2). On further irradiation, 2 is converted into o-benzylphenol (3) and xanthene (4). Equilibrium concentrations of the ...