Photoisomerization of spironaphthalenones and its mechanism

Kasturi, Tirumalai R. ; Mandal, Asish B. ; Prasad, Ganesha K. B. ; Raju, Gonibella J. (1992) Photoisomerization of spironaphthalenones and its mechanism Tetrahedron, 48 (40). pp. 8841-8848. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)89455-2

Abstract

Spironaphthalenones 1a-g & 1j-m on irradiation, with UV light gives the isomeric spironaphthalenones 2a-g & 2j-m in almost quantitative yield. On the other hand, spironaphthalenones 1h, 1i, 1n & 1o photoisomerized to the isomeric spironaphthalenones in reduced yields. Similar irradiation of 2a-g & 2j-m did not bring any change whereas 2h, 2i, 2n & 2o rearranged to isomeric spironaphthalenones. A probable mechanism has been proposed for this isomerization.

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