The preparation and conformation of 1-alkyl- and 1-aryl-4-t-butylcyclohexanols

Abstract

4-t-Butylcyclohexanone and Grignard reagents (RMgHal) give mixtures of 4β- and 4α-t-butyl-1 α-R-cyclohexan-1β-ols in which the percentages of the 4β-compounds (equatorial R groups) are approximately 55 (R = Me), 69 (Et), 82 (Prⁱ), 100 (Bu^t), 49 (Ph), and 80 (CH₂Ph): the mixture of tertiary alcohols from 5α-cholestan-3-one and PhCH₂MgCl contains 83% of the 3β(equatorial)-benzyl compound.

Spectroscopic examination of the products leads to conclusions about the conformations arising from rotation of the hydroxy-groups.