Sulfilimine. I. Synthesis and Formation Mechanism

Abstract The kinetics of the reaction of sulfide and chloramine T was investigated. The reaction was very much affected by pH, and the rate reached the maximum at pH 5.5. The reaction was found to be facilitated by the substitution of an electron-releasing group in phenyl rings of aryl methyl sulfides. From these observations the rate-determining step appears to involve the formation of the sulfonium cation intermediate. From the mechanistic study of this reaction, an effective procedure for the synthesis of sulfilimine was devised.