Journal of the American Chemical Society

Macro rings. XXXV. Stereochemistry of [2.2] paracyclophanyl nucleus as a neighboring group in solvolyses reactions

DJ Cram, FL Harris

Index: Cram,D.J.; Harris,F.L. Journal of the American Chemical Society, 1967 , vol. 89, p. 4642 - 4651

Full Text: HTML

Citation Number: 13

Abstract

Abstract: The effects of the [2.2] paracyclophanyl nucleus on the kinetics and stereochemistry of carbonium reactions at asymmetric carbon atoms QI and/3 to the system have been examined. Hydrolysis in 9: l dioxane-water of the trichloroacetate of the a-and &diastereomers of 4-(l-hydroxyethyl)-[2.2] paracycl0phane both gave 1: 1 mixtures of the corresponding a and, B alcohols, and at rates (first order) that differed by only about 10%. ...