Ojima, Fumihiro;Osa, Tetsuo published 《Perkin-Markovnikov type reaction initiated with electrogenerated superoxide ion》 in 1989. The article was appeared in 《Bulletin of the Chemical Society of Japan》. They have made some progress in their research.Category: esters-buliding-blocks The article mentions the following:
The cyclic condensation of active methylene compounds such as di-Et malonate, di-Me malonate, Et acetoacetate or acetylacetone and dibromoalkanes such as 1,2-dibromobutane, or 1,4-dibromopentane with electrogenerated superoxide ion was studied electrochem. in DMF using cyclic voltammetry (CV) and controlled potential macroelectrolysis. The CV shows that electrogenerated superoxide ion reacts with both active methylene compounds and dibromoalkanes in the dissolved oxygen medium. Controlled potential macroelectrolysis of the above components generally yielded cycloalkanes as the main products. In comparison, the chem. method using sodium ethoxide was also carried out. Two reaction mechanisms via the proton abstraction of active methylene compds, with electrogenerated superoxide ion and via the nucleophilic attack of the superoxide ion on dibromoalkanes are presented. To complete the study, the researchers used Diethyl cyclobutane-1,1-dicarboxylate (cas: 3779-29-1) .
Diethyl 1,1-cyclobutanedicarboxylate(cas:3779-29-1 Category: esters-buliding-blocks) reacts with silicon to form diethyl esters and magnesium to form magnesium salts. The reaction time for this compound is short, which may be due to its ability to undergo debromination.
Reference:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics