Photorearrangements of bridgehead-disubstituted dibenzobarrelene esters and lactones

Ajaya Kumar, S. ; Rajesh, C. S. ; Das, Suresh ; Rath, N. P. ; George, M. V. (1995) Photorearrangements of bridgehead-disubstituted dibenzobarrelene esters and lactones Journal of Photochemistry and Photobiology A: Chemistry, 86 (1-3). pp. 177-183. ISSN 1010-6030

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This study deals with the photorearrangements of a few bridgehead-disubstituted dibenzobarrelene, i.e. dimethyl-9-hydroxymethyl-10-methyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate (1) and the dibenzobarrelene lactone derivatives (10a,b). Irradiation of 1 in benzene gives a 77% yield of a dibenzocyclooctatetraene (8) with C2 symmetry with respect to its substituents. In contrast, the photolysis of 10a yields the dibenzosemibullvalene (15a) in nearly quantitative yield. Similarly, the dibenzobarrelene lactone (10b) undergoes facile photoisomerization to the corresponding dibenzosemibullvalene (15b) in 92% yield. The structures of the photoproducts 8 and 15a have been unambiguously established through X-ray crystallographic analysis.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Photorearrangement; Dibenzobarrelene Esters; Lactones
ID Code:8791
Deposited On:28 Oct 2010 10:51
Last Modified:31 May 2011 07:11

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