Isomerization of N-[α-(Alkylthio)alkyl]- and N-[α-(Arylthio)alkyl]benzotriazoles

✍ Scribed by Alan R. Katritzky; Wojciech Kuzmierkiewic; Subbu Perumal

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: German
• Weight: 246 KB
• Volume: 74
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19910740831

✦ Synopsis

The thermal isomerizations of N-[a -(alkylthio)alkyl]-and N-[a -(arylthio)alkyl]benzotriazoles have been investigated under N, atmospheres i ) in toluene, xylene, MeOH, or EtOH, in the presence of acid catalysts and ii) in the absence of solvent. The sulfide isomerization rates depend on the number of H-atoms carried by the C-atom attached to the N-atom of the benzotriazole: tertiary (no hydrogen) > secondary (1 hydrogen) > primary (2 hydrogens). The results support an isomerization mechanism involving a heterolytic N-C bond cleavage with formation of sulfonium/carbonium and benzotriazolate ions.