OXYMERCURATION OF THE METHYLCYCLOHEXENES

Abstract

It has been found that, while hydroxymercuration of 2-methylcyclohexene leads to a single product, 3-methylcyclohexene gives a nonworkable mixture and 4-methylcyclohexene gives both positional and diastereoisomers of which three of the four have been isolated. The ratio of positional isomers is found to be 5:1 in favor of farthest distance of the methyl group from the mercury atom. The conversion of the chloromercuri-hydroxy-methylcyclohexanes to chloromercuri-methoxy-methylcyclohexanes by potassium tert-butoxide and dimethyl sulphate has been accomplished. Thus the products of hydroxymercuration have been related configurationally to two of the three products of 4-methylcyclohexene methoxymercuration. Among these products that one is most prevalent in which the mercury is most distant, positionally and confjgurationally, from the methyl group in the alkene.