The oxymercuration-demercuration (OM-DM) of several methyl-and tert-butylcyclohexenes and-cyclopentenes has been investigated. The conformationally flexible 4- methylcyclohexene undergoes hydration in a nonregioselective but remarkably stereoselective fashion, giving a 5050 ratio of the trans-3-and cis-4-methylcyclohexanols with only-1% each of the other two isomers. In the case of 3-methylcyclohexene, hydration ...
