AGENTS AFFECTING LIPID METABOLISM: XIII. THE SYNTHESIS OF 1,4-DISUBSTITUTED BICYCLO[2.2.2]OCTANE DERIVATIVES

Abstract

Several routes to the synthesis of 1,4-disubstituted bicyclo[2.2.2]octanes have been explored and the syntheses of several such derivatives are reported. The 1,4-disubstituted bicyclo[2.2.2]-octane nucleus could not be prepared through an elimination reaction on a corresponding 2,5-disubstituted derivative or by the Diels–Alder reaction of various dienophiles with dimethyl 1,3-cyclohexadiene-1,4-dicarboxylate.Unusual products are obtained from the reaction of tetracyanoethylene with dimethyl terephthalate and with 1,3-cyclohexadienes containing electron-attracting groups in the 1,4-positions. Some spectral properties of these compounds are described.