Electroreduction of methyl 2-bromo-2-phenylpropanoate on a vitreous carbon electrode: meso- and DL-dimethyl 2,3-dimethyl-2,3-diphenylsuccinate

Abstract

The electrochemical reduction of ethyl a-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-diethyl2,3-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 MeO2C-CMePh.C6H4.CMeCO2Me-CMePh-C02Me (9). To explain the results, a mechanism is proposed, involving the formation of dimer (10) as an intermediate.

Influence of the Axial Alkyl Ligand on the Reduction Potential of Alkylcob(III)alamins and Alkylcob(III)yrinates

“…Estimated from the corresponding ethyl ester, measured in 0 . 1~ Et4NCI04/DMF at 200 mV/s [38]. Value for the corresponding ethyl esters.…”

The synthesis and stereospecific solid-state photodecarbonylation of hexasubstituted meso- and d,l-ketones

“…Unfortunately, ultraviolet irradiation of d,l-2d in the solid-state was also expected to give a mixture of product since the predicted recombination product d,l-5d is known to be an oil. 22 Indeed, the sample of d,l-2d began melting almost as soon as the photolysis started. Quite notably, the reaction was more selective towards radical disproportionation while the formation of recombination products was inefficient and with low stereoselectivity (Table 3).…”

“…The solution photolysis of the keto diester d,l-2d gave a larger number of products including diesters d,l-5d and meso-5d, 22 and disproportionation products 1d and 6d. Interestingly, acrylate 6d was observed in the 1 H NMR at low conversions but disappeared over time, presumably due to in situ polymerization.…”

Chapter 6. Electro-organic chemistry

“…Morphinandienones (41) of the flavinantine type are obtained in high yield via the anodic coupling of Ntrifluoroacetyl-l-benzyl-l,2,3,4-tetrahydroisoquinolines (39) in acetonitrile-methanol solution, but when the methanol is omitted neos- Should 0-methylflavinantine (43) itself be oxidized in acidic solution the 10ahydroxy derivative (44) is obtained together with the pentacycle (45). The formation of these two products is considered to be interrelated as indicated in Scheme…”

“…41) of the flavinantine type are obtained in high yield via the anodic coupling of Ntrifluoroacetyl-l-benzyl-l,2,3,4-tetrahydroisoquinolines(39) in acetonitrile-methanol solution, but when the methanol is omitted neos-31 S. Torii, H. Tanaku, N. Saitoh, T. Siroi, M. Sasaoka, and J. Nokami, Terruhedron Lert,, 1981, 22, 3193. 32 S. Torii, H. Tanaku, N. Saitoh, T. Siroi, M. Sasaoka, and J. Nokami, Tetrahedron Lett., 1982,23, 2187; 33 E.-C. Lin and M. R. Van de Mark, J. Chem.…”