Issue 7, 1982

The photochemistry of 2-vinyldiphenylacetylene and related compounds

Abstract

Irradiation of solutions of 2-vinyldiphenylacetylene (5) under anaerobic conditions gives 2-phenylnaphthalene (9) in 90% yield. Several derivatives of (5) behave similarly. The reaction is ascribed to the primary formation of a cyclic allene (29), as has been proposed previously for the analogous photocyclization of 1,4-diarylbutenynes into phenylaromatic compounds. The end-product arises from (29) either via a 1,5-hydrogen shift or by addition and elimination of a proton. Irradiation of 2-ethynylstilbene (21) also yields (9), but 1-ethynylphenanthrene (22) is formed as a side-product.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1982, 795-799

The photochemistry of 2-vinyldiphenylacetylene and related compounds

P. M. op den Brouw and W. H. Laarhoven, J. Chem. Soc., Perkin Trans. 2, 1982, 795 DOI: 10.1039/P29820000795

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