Tetrahedron

Substituent effects on the regio-and stereoselectivity of gas-phase acid-induced ring opening in 1-arylcyclohexene oxides

P Cecchi, A Pizzabiocca, G Renzi, M Chini, P Crotti…

Index: Cecchi, P.; Pizzabiocca, A.; Renzi,G.; Chini, M.; Crotti, P.; et al. Tetrahedron, 1989 , vol. 45, # 13 p. 4227 - 4234

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Citation Number: 10

Abstract

Comparative analysis of the ratio of the isomeric monomethyl ethers of 1-arylcyclohexane-1, 2-diols formed in the gas-phase and solvalytic acid-induced methanolysis of several 1- arylcyclohexene oxides indicates the intrinsic electronic factors determining the regio-and stereochemical course of the nucleophilic attack, related to the partial degree of carbocationic character at the reaction centre in the substitution transition state.