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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Photochemical syntheses. III. The synthesis and photo-isomerization of 1,2-Diphenyl-2a,8b-dihydrocyclobuta[a]naphthalene and some derivatives

PJ Collin and WHF Sasse

Australian Journal of Chemistry 24(11) 2325 - 2338
Published: 1971

Abstract

Fourteen derivatives of the naphthalene-diphenylacetylene photo-adduct (1a) have been thermally isomerized to give high yields of derivatives of 1,2-diphenyl-2a,8b-dihydrocyclobuta[a]naphthalene (1b). Of these only the 4-methoxy derivative (13b) could be rearranged to the isomeric benzocyclooctatetraene (13c). Five alkyl and one methoxy derivative of (1b) were quantitatively isomerized to derivatives of (1a) but the isomerization of the esters (10b) and (11b) gave mixtures. Photo-iso- merization of the methoxybenzocyclooctatetraene (13c) gave exclusively (13b) and (13a).     Mechanistic aspects of these reactions are discussed.

https://doi.org/10.1071/CH9712325

© CSIRO 1971

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