Phototransformations of 9-ethyl-substituted dibenzobarrelene  

Mathew, Thomas ; Kumar, S. Ajaya ; Das, Suresh ; Rath, N. P. ; George, M. V. (1996) Phototransformations of 9-ethyl-substituted dibenzobarrelene   Journal of Photochemistry and Photobiology A: Chemistry, 95 (2). pp. 137-141. ISSN 1010-6030

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Photolysis of 11,112-dibenzoyl-9, 10-dihydro-9-ethyl-9,10-ethenoanthracene (1) in benzene or acetone in the complete absence of oxygen gives the 4b-ethyl-substituted dibenzosemibullvalene ( 5) (45-48%) whereas, in the presence of oxygen, 1 in acetone gives a mixture of 5 (32%), together with two oxygenated products, namely the peroxy compound 12 and the lactone 20. The structures of 5, 12 and 20 have been confirmed through single-crystal X-ray diffraction studies. Compound 5 arises through a di-p-methane rearrangement of 1, whereas 12 is formed through the oxygen quenching of a diradical intermediate, derived from an isomeric 8b-ethyl-substituted dibenzosemibullvalene (6). Compound 20 arises through the oxygen quenching of a diradical intermediate, implicated in the photorearrangements of 1,2-dibenzoylalkenes.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Phototransformations; Dibenzosemibullvalenes; X-ray Diffraction; Oxygen-quenching
ID Code:12659
Deposited On:12 Nov 2010 15:35
Last Modified:31 May 2011 07:02

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