Six-fold rotational potentials in substituted ethanes; a dynamic n.m.r. study of tri-t-alkylmethanols

Abstract

Contrary to conventional thinking about carbon–carbon single bonds, there are six different locations for a methyl group and six equivalent conformations during 360° rotation of a t-butyl group in adamantyldi-t-butylmethanol; there is a high barrier to passage through an eclipsed conformation (rotation), and an almost as high barrier to passage through perfectly staggered transition states (libration); similar results obtained for other methanols R¹R²R³COH (R = adamantyl or t-butyl).