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Mechanism of oxidation of α,β-unsaturated thiones by singlet oxygen

Rao, V Pushkara and Ramamurthy, V (1985) Mechanism of oxidation of α,β-unsaturated thiones by singlet oxygen. In: Tetrahedron, 41 (11). pp. 2169-2176.

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Photo-oxidation of α,β-unsaturated thiones yields the corresponding ketones as the only product. Studies carried out on three systems, namely thioketones, α,β-unsaturated thiones and thioketenes, have revealed that there exists a similarity in their mechanism of oxidation. It has been suggested that the thiocarbonyl chromophore is the site of attack by singlet oxygen in α,β-unsaturated thiones and that the adjacent C-C double bond is inert under these conditions. Absence of sulphine during the oxidation of α,β-unsaturated thiones is attributed to the electronic factors operating on the zwitterionic/diradical intermediate. While α,β-unsaturated ketones are poorly reactive, α,β-unsaturated thiones are highly reactive toward singlet oxygen.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: The copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 24 Nov 2009 10:09
Last Modified: 19 Sep 2010 05:35
URI: http://eprints.iisc.ac.in/id/eprint/20967

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