Abstract
AbstractThe stereoselectivity of a series of 1‐aryl‐1,2‐epoxycyclohexanes substituted on the phenyl group was determined in acid methanolysis in the condensed phase (0.2 N H2SO4–MeOH) and in the reaction with MeOH in the gas phase under catalysis by a gaseous Brønsted acid (D3+). The results obtained show the presence of a clear Hammett‐type dependence of the syn/anti adduct ratio on the Brown σ+ of the substituent on the phenyl group, thus confirming the validity of the ion–dipole pair mechanism in order to rationalize the stereochemical behavior of 2‐aryloxiranes in opening reactions under acidic conditions. Only in the cases of the p‐OMe‐ and p‐NO2‐substituted epoxides, does an SN1 and an SN2 process, respectively, appear to be involved. Copyright © 2004 John Wiley & Sons, Ltd.
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