Electrochemical reactions. Part IX. Reduction of 2-acetylnaphthalene. Stereochemistry of the isomeric 2,3-di-(2-naphthyl)butane-2,3-diols

Abstract

Electrochemical reduction of 2-acetylnaphthalene gives the isomeric 2,3-di-(2-naphthyl)butane-2,3-diols in good yield. The (±)-isomer is formed in greater amount, with degree of stereoselectivity 0·27 in alkaline and 0·09 in acid solution. Synthesis of these diols from a diketone and 2-naphthylmagnesium bromide or methyl-lithium obeys Cram's rule with high stereoselectivity. Stereochemical assignments to the diols are made by an n.m.r. method.