Steric hindrance of resonance in a substituted phenylmethylsulphone: (Properties of the sulphonyl group XXXVIII)

Autor: H. J. Backer, H. Kloosterziel
Rok vydání: 2010
Předmět:
Zdroj: Recueil des Travaux Chimiques des Pays-Bas. 72:655-659
ISSN: 0165-0513
DOI: 10.1002/recl.19530720804
Popis: N-acetyl-4-methylsulphonyl-2,6-xylidine (I) has been prepared by the convenient method used before, involving thiocyanation of 2,6-xylidine and reduction of the thiocyano group with LiAlH4, followed by methylation and subsequent oxidation of N-acetyl-4-methylmercapto-2,6-xylidine to the corresponding sulphone. The latter compound (I) has an U.V. spectrum intermediate between those of phenylmethylsulphone and N-acetyl-p-methylsulphonylaniline, indicating that the extended resonance is sterically hindered.
Databáze: OpenAIRE