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Direct Conversion of tert-‚-Bromo Alcohols to Ketones with Zinc Sulfide and DMSO

Bettadaiah, B. K. and Gurudutt, K. N. and Srinivas, P. (2003) Direct Conversion of tert-‚-Bromo Alcohols to Ketones with Zinc Sulfide and DMSO. Journal of Organic Chemistry, 68. pp. 2460-2462.

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Abstract

tert-β-Bromo alcohols, derived from simple monoterpene hydrocarbons, react with zinc sulfide in dimethyl sulfoxide to afford saturated ketones as the major and hydroxy ketones as the minor products. The reaction involves initial nucleophilic attack by DMSO on the carbon attached to the halogen, which is assisted by electrophilic zinc sulfide. Subsequent Kornblum type oxidation yields the R-hydroxy ketone. On the other hand, abstraction of proton ‚ to the hydroxyl group followed by an attack of the neighboring hydroxyl moiety on the sulfur of the imethylsulfoxonium intermediate and its subsequent collapse yields an enol, which tautomerizes to a saturated ketone. The latter pathway is predominantly followed.

Item Type: Article
Uncontrolled Keywords: tert-β-Bromo alcohols bromohydrins DMSO
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 24 Organic Chemistry
Divisions: Plantation Products Spices and Flavour Technology
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 10 Jan 2008 05:56
Last Modified: 28 Dec 2011 09:32
URI: http://ir.cftri.com/id/eprint/1628

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