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Issue 11, 2005
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Photochemical rearrangement of dibenzo[1,4]dioxins proceeds through reactive spirocyclohexadienone and biphenylquinone intermediates

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Abstract

Photochemical studies on a range of model dibenzo[1,4]dioxins were performed in aqueous and organic solutions. The compounds were found to undergo a photochemically initiated aryl–ether bond homolysis that yields reactive 2-spiro-6′-cyclohexa-2′,4′-dien-1′-one and subsequent 2,2′-biphenylquinone intermediates. Under steady-state irradiation, the 2,2′-biphenylquinones were observed to participate in excited state hydrogen abstraction from the organic solvent to give the corresponding 2,2′-dihydroxybiphenyls. In the absence of continued irradiation, 2,2′-biphenylquinones with electron donating substituents thermally rearrange to the corresponding oxepino[2,3-b]benzofurans, whereas the unsubstituted 2,2′-biphenylquinone and its derivatives with electron withdrawing groups thermally rearrange to the corresponding 1-hydroxydibenzofurans.

Graphical abstract: Photochemical rearrangement of dibenzo[1,4]dioxins proceeds through reactive spirocyclohexadienone and biphenylquinone intermediates

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Supplementary files

Article information


Submitted
14 Apr 2005
Accepted
11 Aug 2005
First published
09 Sep 2005

Photochem. Photobiol. Sci., 2005,4, 876-886
Article type
Paper

Photochemical rearrangement of dibenzo[1,4]dioxins proceeds through reactive spirocyclohexadienone and biphenylquinone intermediates

S. Rayne, R. Sasaki and P. Wan, Photochem. Photobiol. Sci., 2005, 4, 876
DOI: 10.1039/B505244K

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