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

Photochemical syntheses. IV.The formation of 1-Alkoxynaphthalene-diphenylacetylene photo-adducts and their acid-catalysed hydrolysis. A new route to 2a, 8b-Dihydrocyclobuta[α]naphthalenes

WHF Sasse, PJ Collin, DB Roberts and G Sugowdz

Australian Journal of Chemistry 24(11) 2339 - 2346
Published: 1971

Abstract

1-Methoxy-, 1-ethoxy-, and 1-isopropoxy-naphthalene react with diphenyl- acetylene (dpa) to give the photo-adducts (2), (3), and (4) in 90-95% yield. The adducts (5), (6), and (7) each account for less than 1%. Each 1-alkoxynaphthalene gives also less than 5% of ketone (10) which is formed also by hydrolysis of two 4-alkoxy-1,2-diphenyl- 2a,8b-dihydrocyclobuta[a]naphthalenes. Several 2-substituted naphthalene-dpa photo-adducts rearrange in the presence of acid quantitatively into 4-substituted 1,2-diphenyl-2a,8b-dihydrocyclobuta[a]naphthalenes Likely intermediates in these rearrangements are discussed. 2-Methoxy-, 2-ethoxy-, and 2-isopropoxy- naphthalene do not add dpa. The first two compounds form photodimers but 2-isopropoxynaphthalene does not do so, and photo-dimerization is not the cause of the failure of 2-alkoxynaphthalenes to add dpa.

https://doi.org/10.1071/CH9712339

© CSIRO 1971

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