Preparation of N-Alkyl-S,S-diphenylsulfimides by the Reaction of N-Unsubstituted S,S-Diphenylsulfimide with Borane-Pyridine

Abstract

The reaction of an N-unsubstituted S,S-diphenyl­sulfimide [1] with aldehydes or ketones in the presence of a borane-pyridine complex and acetic acid in benzene at 40 °C affords the corresponding N-alkyl-S,S-diphenylsulfimides. Since this reaction does not form the N,N-dialkylated aminosulfonium salt, this method provides a convenient preparation of N-monoalkylsulfimides without the necessity for a difficult separation of the products by column chromatography due to their similar R _f values. The mechanism of formation is discussed.

Key words

N-alkyl-S,S-diphenylsulfimides - borane-pyridine - monoalkylation - N-unsubstituted S,S-diphenylsulfimide

References

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