. alpha.-Carbon-sulfur oxidation-reduction reactions of sulfoxides. The case of benzylic sulfoxides

DA Davenport, DB Moss, JE Rhodes…

Index: Davenport,D.A. et al. Journal of Organic Chemistry, 1969 , vol. 34, # 11 p. 3353 - 3359

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Citation Number: 9

Abstract

In refluxing glacial acetic acid, a-(benzylsulfinyl)-p-nitrotoluene (1) readily gives a, a-di (benzylthio)-pnitrotoluene (2) and p-nitrobenzaldehyde (4), while benzyl sulfoxide (6) and phenyl benzyl sulfoxide (8) are unreactive. In contrast, 1, 6, and 8 all undergo redox reactions with hydrogen chloride in dry ether or alcohol. Isotope dilution analysis shows that, with hydrogen chloride in ether, 1 forms both 2 and ala-di (p-nitrobenzylthio) toluene (3) in ...