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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis of Bridgehead-Bridgehead Substituted Bicycloalkanes

EW Della and J Tsanaktsidis

Australian Journal of Chemistry 38(11) 1705 - 1718
Published: 1985

Abstract

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.

https://doi.org/10.1071/CH9851705

© CSIRO 1985

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