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Isomerization of N ‐[α‐(Alkylthio)alkyl]‐ and N ‐[α‐(Arylthio)alkyl]benzotriazoles
Author(s) -
Katritzky Alan R.,
Kuzmierkiewic Wojciech,
Perumal Subbu
Publication year - 1991
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19910740831
Subject(s) - chemistry , sulfonium , alkyl , isomerization , medicinal chemistry , carbonium ion , heterolysis , toluene , hydrogen atom , bond cleavage , photochemistry , catalysis , organic chemistry , salt (chemistry)
Abstract The thermal isomerizations of N ‐[α‐(alkylthio)alkyl]‐ and N ‐[α‐(arylthio)alkyl]benzotriazoles have been investigated under N 2 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.