Abstract
AbstractThe thermal isomerizations of N‐[α‐(alkylthio)alkyl]‐ and N‐[α‐(arylthio)alkyl]benzotriazoles have been investigated under N2 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 isomenzation mechanism involving a heterolytic NC bond cleavage with formation of sulfonium/carbonium and benzotriazolate ions.
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