Alkanesulfonylation. XIII. Solvation effects of the solvent on the competing mechanisms of alkanesulfonylation of phenol under conditions of catalysis by tertiary amines

Journal Article · Sun Nov 20 00:00:00 EST 1988 · J. Org. Chem. USSR (Engl. Transl.); (United States)

OSTI ID:5887770

Bezrodnyi, V P; Lyashchuk, S N; Skrypnik, Yu G

Change in the nature of the solvent leads to a significant change in the ratio of the competing mechanisms in alkanesulfonylation, i.e., the sulfene (1a) and general base catalysis (1b). The most important role here is played by the polarity of the medium, and with increase in the polarity the predominant path changes from (1b) to (1a). In the case of mechanism (1b) the effects of specific solvation show up more strongly than for mechanism (1a). This is due to differences in the structure of the transition states. A quantitative assessment of the solvation effects on the rate of the competing paths (1a, b) is given.

• Research Organization: Institute of Physical Organic Chemistry and Coal Chemistry, Donetsk (USSR)
• OSTI ID: 5887770
• Journal Information: J. Org. Chem. USSR (Engl. Transl.); (United States), Vol. 24:6; Other Information: Translated from Zh. Org. Khim.; 24: No. 6 1253-1258 (Jun 1988)
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
AMINES
CATALYTIC EFFECTS
ORGANIC SOLVENTS
SOLVENT PROPERTIES
PHENOL
SOLVATION
ACETIC ACID ESTERS
ACETONITRILE
ALKYLATION
BENZENE
CATALYSIS
CATALYSTS
CHEMICAL REACTION KINETICS
CHLORINATED AROMATIC HYDROCARBONS
CHLOROFORM
CYCLOHEXANONE
KINETIC EQUATIONS
METHYLENE CHLORIDE
NITROBENZENE
POTENTIOMETRY
REGRESSION ANALYSIS
SULFONATION
TOLUENE
XYLENE-PARA
XYLENES
ALKYLATED AROMATICS
AROMATICS
CARBOXYLIC ACID ESTERS
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
EQUATIONS
ESTERS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HYDROCARBONS
HYDROXY COMPOUNDS
KETONES
KINETICS
MATHEMATICS
NITRILES
NITRO COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHENOLS
REACTION KINETICS
SOLVENTS
STATISTICS
TITRATION
400201* - Chemical & Physicochemical Properties