Reactivity of groups attached to reduced cyclic ring systems—I : Kinetics of the menschutkin reaction of 3-dimethylaminomethyl steroids with methyl iodide, and consideration of the reasons for the observed differential rates in some other reactions at epimeric axial and equatorial grousps

Abstract

In contrast to the previously examined 2 epimeric dimethylamino steroids, spimeric dimethylaminomethyl steroids (containing the group CH 2NMe 2) react at approximately the same rates with methyl iodide in nitrobenzene-benzene. This observation is significant for the consideration of differential reactivity in other reactions with epimeric axial-equatorial pairs: the relative ease of hydrolysis of esters of epimeric axil and equatorial alcohols, for example, is probably due mainly to differential hindrance to solvation at the relevant alkoxy oxygen atoms during reaction.