Synthesis of Aryl Ethers by Nonactivated Aromatic Nucleophilic Substitution Reactions.

Mil'to, V. I.; Orlov, V. Yu.; Mironov, G. S.

The results of a kinetic study of model reactions between substituted phenols and bromobenzene in the presence of potassium carbonate and the copper(I) chloride–8-hydroxyquinoline catalytic complex in N,N-dimethylformamide are presented. The reactions were found to obey a first-order rate law. Both orbital and charge interactions should be taken into account in a consideration of the effect of the structural characteristics of reactants on the rate of reaction. The kinetics of substitution of the phenoxide anion for an aromatically bound halogen atom in activated and nonactivated systems with the formation of practically valuable aryl ethers were comparatively studied. The results presented provide an opportunity to distinguish the common features and regularities of activated and nonactivated aromatic substitution in the test systems.

ESTERS; PHENOLS; COPPER; CATALYSIS; HALOGENS; DIMETHYLFORMAMIDE

Kinetics & Catalysis, 2003, Vol 44, Issue 6, p747

0023-1584

Academic Journal

10.1023/B:KICA.0000009048.91557.ff