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Photochemical Oxidation of Thioketones: Steric and Electronic Aspects

Ramanath, N and Ramesh, V and Ramamurthy, V (1983) Photochemical Oxidation of Thioketones: Steric and Electronic Aspects. In: Journal of Organic Chemistry, 48 (2). pp. 214-222.

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Oxidation of diaryl, aryl alkyl, and dialkyl thioketones by singlet oxygen generated via self-sensitization and other independent methods yielded the corresponding ketone and sulfine in varying amounts. A zwitterionic/ diradical intermediate arising out of the primary interaction of singlet oxygen with the thiocarbonyl chromophore is believed to be the common intermediate for the ketone and sulfine. While closure of the zwitterion/diradical to give 1,2,3-dioxathietane would lead to the ketone, competing oxygen elimination is believed to lead to the sulfine. This partitioning is governed by steric and electronic factors operating on the zwitterionic/diradical intermediate.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: American Chemical Society
Additional Information: copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Feb 2010 06:28
Last Modified: 19 Sep 2010 05:36
URI: http://eprints.iisc.ac.in/id/eprint/21167

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