ISSN:
1042-7163
Keywords:
Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The oxidation of a series of ketene-S,S-acetals, 2a-f, and a series of thioacetals and thioketals, 4a-g, with a fourfold or greater excess of dimethyldioxirane, 1, produced the corresponding bis-sulfones 3a-f and 5a-g in excellent yields. The reaction of the bis-sulfides with one, two, and three equivalents of 1 yielded monosulfoxides, bis-sulfoxides, and sulfoxide-sulfones, respectively, as the major products. The order of addition of the reactants as well as the temperature of the reaction mixture changed the product distributions. The use of low-temperature, rapid stirring and the addition of the dioxirane solution to the bis-sulfide maximized the yield of the major product. The results are consistent with an electrophilic oxygen-atom transfer mechanism in which the rate of sulfide oxidation is much faster than oxidation of sulfoxide to sulfone. However, sulfoxide oxidation is of a sufficient rate such that local concentration effects affect the results.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hc.520050522
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