Base-induced proton tautomerism in the primary photocyclization product of stilbenes

…, A Lablache-Combier, WH Laarhoven

Index: Somers, J. B. M.; Couture, A.; Lablache-Combier, A.; Laarhoven, W. H. Journal of the American Chemical Society, 1985 , vol. 107, # 5 p. 1387 - 1394

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Citation Number: 26

Abstract

Abstract: The mechanism of the photoformation of 1, 4-dihydrophenanthrenes (1, 4-DHP) and 9, lO-dihydrophenanthrenes from 1, 2-diarylethylenes in amine solution is clarified by demonstrating that the amine reacts as a base with the initially formed 4a, 4b- dihydrophenanthrene. The predominant formation of 1, 4-DHP from stilbene is ascribed to an easy proton transfer from C (4b) to C (4) in 4a, 4b-DHP via a deprotonation/protonation ...