Abstract
Abstract When diaryl sulfoxides are dissolved in concentrated sulfuric acid at 0°C, characteristic bluish colored solutions are obtained, from which the starting sulfoxides can be recovered quantitatively upon quenching with a large amount of water. When 18O-labeled and optically active sulfoxides are used, one observes the concurrent oxygen exchange and racemization reactions of the sulfoxides. The kinetic behaviors of these reactions have been studied in detail using various substituted diaryl sulfoxides. The rate of the oxygen exchange was found to be identical to that of the racemization while the rates of the racemization were nicely correlated with the Hammett acidity functions (H0) (Slope=1.07). Meanwhile the polar effect of subsituents on the rates of both oxygen exchange and racemization was found to be very small. From these results possible mechanisms for these reactions have been discussed.
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