Ramnath, N. ; Ramesh, V. ; Ramamurthy, V. (1983) Photochemical oxidation of thio ketones: steric and electronic aspects Journal of Organic Chemistry, 48 (2). pp. 214-222. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00150a015
Related URL: http://dx.doi.org/10.1021/jo00150a015
Abstract
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: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 55539 |
| Deposited On: | 18 Aug 2011 11:35 |
| Last Modified: | 19 Aug 2011 06:07 |
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