84892-16-0Relevant academic research and scientific papers
Electroreduction of Methyl 2-Bromo-2-phenylpropanoate on a Vitreous Carbon Electrode: meso- and DL-Dimethyl 2,3-Dimethyl-2,3-diphenylsuccinate
Luca, Carlo de,Inesi, Achille,Rampazzo, Liliana
, p. 1403 - 1408 (2007/10/02)
The electrochemical reduction of ethyl α-bromophenylacetate (1) and methyl 2-bromo-2-phenylpropanoate (5) in dry dimethylformamide on a vitreous carbon electrode has been studied.Dimeric products are formed as a consequence of controlled potential electrolysis of (1) and (5) on a reticulated vitreous carbon electrode.By this route, meso- and DL-diethyl 2,3-diphenylsuccinate and -dimethyl 2,3-dimethyl-2,3-diphenylsuccinate are obtained from ester (1) and (5), respectively.A triester is also obtained among the products.The spectral data (n.m.r., mass spectra) show the structure of this triester to be almost certainly MeO2CCMePhC6H4CMeCO2MeCMePhCO2Me (9).To explain the results, a mechanism is proposed, involving the formation of dimer (10) as an intermediate.
