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Oxidations of thio ketones by singlet and triplet oxygen

Rao, V Jayathirtha and Muthuramu, K and Ramamurthy, V (1982) Oxidations of thio ketones by singlet and triplet oxygen. In: Journal of Organic Chemistry, 47 (1). pp. 127-131.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00340a027


Oxidation of di-tert-butyl thioketone (1) and 2,2,4,4-tetramethylcyclobutylth ioketone (2) by singlet oxygen yields the corresponding sulfine and ketone; in the case of 1 the sulfine is the major product, whereas in 2 it is the ketone. 1,2,3-Dioxathietane has been suggested as the precursor for the ketones, and the zwitterionic/diradid peroxide is believed to be a common primary intermediate for both sulfine and ketone. Steric influence is felt both during primary interaction between singlet oxygen and thioketone and during the partitioning of the peroxide intermediate. Steric interaction is suggested as the reason for variations in the product distribution between 1 and 2. Singlet oxygen is also generated through energy transfer from the triplet state of thioketones. These excited states also directly react with oxygen to yield ketone.

Item Type: Journal Article
Publication: Journal of Organic Chemistry
Publisher: ACS Publications
Additional Information: Copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 14 Dec 2009 06:00
Last Modified: 19 Sep 2010 05:47
URI: http://eprints.iisc.ac.in/id/eprint/23748

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