PREPARATION AND CONFORMATIONS OF 1-ALKYL- AND 1-ARYL-4-T-BUTYLCYCLOHEXANOLS

4-t-Butylcyclohexanone and Grignard reagents (RMgHal) give mixtures of 4β- and 4α-t-butyl-1α-R-cyclohexan-1β-ols in which the percentages of the 4β-compounds (equatorial R groups) are approximately 55 (R = Me), 69 (Et), 82 (Pr1), 100 (But), 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.