Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Oxygen Exchange Reaction of Sulfoxides in Dinitrogen Tetroxide
Norio KuniedaKazuo SakaiShigeru Oae
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1969 Volume 42 Issue 4 Pages 1090-1094


Sulfoxides are known to undergo concurrent oxygen exchange and racemization reactions with various reagents (Bull. Chem. Soc. Japan, 41, 1025 (1968)). Especially well studied are the oxygen exchange reactions in acid media. We have found a similar concurrent oxygen exchange and racemization reaction of sulfoxides with liquid dinitrogen tetroxide. The pseudo first order reaction rates of both oxygen exchange and racemization reactions have been determined using both optically active and 18O-labeled sulfoxides. The kexkrac value was found to be unity, and the polar effect of substituents on the rates of oxygen exchange of substituted diphenyl sulfoxides was found to be considerably large, and correlated with σ+ values with ρ=−1.30. From these results a plausible mechanism for this reaction has been discussed.

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