The Structure and Reactions of (Phenythydrazonomethylthio)alkanes

Abstract

The structure and reactions of (phenylhydrazonomethylthio)alkanes (-N-N=CH-S-) were investigated and compared with those of (phenyliminomethylthio)alkane (-N=CH-S-). (Phenylhydrazonomethythio)alkanes were prepared by the reaction of (methylphenylhydrazono)methanethiol with alkyl halide. The structure of (phenylhydrazonomethylthio)alkane was investigated by ¹H-NMR, ¹³C-NMR, IR and UV spectroscopies and extended Hiickel molecular orbital calculations. (Methylphenylhydrazonomethylthio)ethane [2 a] and (phenyliminothylthio)ethane [1 a] were allowed to react with electrophilic, nucleophilic and oxidative reagents. The results were discussed in terms of different degree and mode of resonance stabilization of (phenylhydrazonomethylthio)alkane and (phenyliminomethylthio)alkane.