10307-22-9Relevant articles and documents
ALKANESULFONYLATION REACTIONS. I. CHARACTERISTICS OF THE ALKANESULFONYLATION OF PHENOL-d1 AND METHANOL-d1 CATALYZED BY TERTIARY AMINES
Skrypnik, Yu. G.,Bezrodnyi, V. P.
, p. 511 - 515 (2007/10/02)
The products from alkanesulfonylation of phenol-d1 and methanol-d1 catalyzed by tertiary amines, which occurs in at least three competing directions (nucleophilic and general base catalysis and a sulfene mechanism), were investigated.The degree of realization of the sulfene mechanism was determined from the content of the ester-d1, and its dependence on the structure of the catalysis, the substrate, the reagent, and the nature of the solvent was investigated.It was shown that the fraction of the ester-d1 decreases with decrease in the basicity and steric accessibility of the tertiary amine.Investigation of the effect of the structure of the sulfonyl chloride shows that the fraction of the sulfene mechanism decreases with decrease in the acidity of the α-protons and their steric accessibility.It was shown that the most favorable conditions for realization of the sulfene mechanism are created in benzene.