57865-04-0Relevant articles and documents
ALKANESULFONATION REACTIONS. XIX. STUDY OF THE COMPETING MECHANISMS IN THE PYRIDINE-CATALYZED PHEN-OLYSIS OF BENZYLSULFONYL CHLORIDE. EFFECT OF REAGENT STRUCTURE
Skrypnik, Yu. G.,Lyahchuk, S. N.,Bezrodnyi, V. P.,Kalmykova, N. Yu.
, p. 1157 - 1164 (2007/10/02)
Gas-liquid chromatography and potentiometric titration were used for the first study of the kinetics of the reaction of a broad range of substituted phenols XC6H4OH with benzylsulfonyl chloride in the presence of pyridine in chlorobenzene at 30 deg C.This reaction proceeds through two competing pathways, namely, elimination-addition (A) and general base catalysis (B).The mesomeric and induction effects of the substituent X were quantitatively determined for pathway B and the predominance of the inductive effect was demonstrated (ρ0 0.828, ρ+ 0.214).The criteria were determined for realization of the competing pathways depending on the phenol structure, including steric hindered structures.The effect of reagent-intermediate orientation was determined in the case of pathway A.
