Making full use of the oxidizing equivalents in bromate in the selective oxidation of thiols, sulfides, and benzylic/secondary alcohols into disulfides, sulfoxides, and aldehydes/ketones

Joshi, Girdhar ; Bhadra, Sukalyan ; Ghosh, Sudip ; Agrawal, Manoj K. ; Ganguly, Bishwajit ; Adimurthy, Subbarayappa ; Ghosh, Pushpito K. ; Ranu, Brindaban C. (2010) Making full use of the oxidizing equivalents in bromate in the selective oxidation of thiols, sulfides, and benzylic/secondary alcohols into disulfides, sulfoxides, and aldehydes/ketones Industrial & Engineering Chemistry Research, 49 (3). 1236–1241. ISSN 0888-5885

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ie901426t

Related URL: http://dx.doi.org/10.1021/ie901426t

Abstract

The oxidation of thiols to disulfides was achieved in high yields with 6:1 mol ratio of thiol to NaBrO3, while the oxidation of sulfides and benzylic/secondary alcohols to the corresponding sulfoxides and aldehydes/ketones was successfully undertaken with 3:1 mol ratio of substrate to NaBrO3. These ratios correspond to the minimum theoretical requirement of NaBrO3. The reactions were conducted at 0-30°C, depending upon substrate, and were initiated with catalytic amounts of H+ and Br (initial Br/BrO3 = 1:3.5 for thiol oxidation and 1:8 for sulfide and alcohol oxidation). Further, regeneration and reuse of the spent reagent in the aqueous effluent was demonstrated.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:41422
Deposited On:30 May 2011 05:36
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