The solvolysis of optically active trans-2-hydroxymethylcyclohexyl brosylate yields trans-2- hydroxymethylcyclohexanol with complete retention of optical activity. This result may be attributed to the intervention of a four-membered oxonium ion intermediate or reaction of the carbonium ion with solvent before any conformational change. The solvolyses of trans-2- hydroxymethylcyclopentyl 8-naphthalenesulfonate and threo-l-hydroxy-2-methyl-3-butyl p- ...
