Effect of substituents on the stereoselectivity of the acid-catalysed hydrolysis of a series of aryloxirans. A new application of the Hammett equation
Abstract
Correlation of the logarithms of the ratios of cis to trans diols formed in the acid-catalysed hydrolysis of 13 1-arylcyclohexene oxides with the σ+ constants indicates that there is a higher degree of carbocationic character in the transition state leading to the cis-product.