
%0 Journal Article
%A Della, EW 
%A Tsanaktsidis, J 
%T Synthesis of Bridgehead-Bridgehead Substituted Bicycloalkanes
%J Australian Journal of Chemistry
%D 1985/11/01
%V 38
%N 11
%P 1705-1718
%K 
%R https://doi.org/10.1071/CH9851705
%U https://www.publish.csiro.au/paper/CH9851705 
%X A convenient synthetic route to several bicycloalkanes bearing substitution at both bridgehead positions is described. The two-step procedure, which involves alkylation of the monoenolates of readily available cyclohexane diesters with 1,2-dihaloethane followed by a base-induced cyclization of the derived haloethylated product, was successfully applied to the synthesis of dimethyl bicyclo[2.2.2]octane- 1,4-dicarboxylate, dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate and dimethyl bicyclo[3.2.1]octane-1,5-dicarboxylate. Additionally, it was found that the two latter diesters could be obtained in quite acceptable yields in a one-pot procedure through their corresponding cyclohexyl bisenolate precursors. 
