Synthesis and configurational and conformational study of the diastereoisomeric 2-(α-hydroxybenzyl)- and 2-(α-methoxybenzyl)-cyclohexanols and some of their derivatives

Abstract

All the diastereoisomeric 2-(α-hydroxybenzyl)-(3), (4), (13), and (14) and 2-(α-methoxybenzyl)cyclohexanols (5), (6), (15), and (16) have been synthesized and some of their derivatives prepared as model compounds of the products of ring opening of some cyclopropanes with electrophiles. The cis–trans configuration and the erythro–threo relationship for all the title compounds have been unequivocally determined by ¹H n.m.r. spectroscopy and by i.r. investigations in the 3 700–3 400 cm^–1 range in dilute solution. These studies also give information about the conformational equilibria around the bond between the benzylic carbon and the cyclohexane ring in this class of products.