Murakami, Yukito published the artcileHydrophobic vitamin B12. V. Electrochemical carbon-skeleton rearrangement as catalyzed by hydrophobic vitamin B12. Reaction mechanisms and migratory aptitude of functional groups, SDS of cas: 56970-78-6, the publication is Bulletin of the Chemical Society of Japan (1987), 60(1), 311-24, database is CAplus.
The C-skeleton rearrangements catalyzed by heptamethyl cobyrinate perchlorate (I) were investigated under electrochem. conditions. The controlled-potential electrolysis of 2,2-bis(ethoxycarbonyl)-1-bromopropane, which is considered to be a model substrate for methylmalonyl-CoA mutase, was catalyzed by I in DMF to give 1,2-bis(ethoxycarbonyl)propane as a major product at -1.5 V vs. SCE (standard C electrode)in the presence of acetic acid and at potentials more cathodic than -1.8 V vs. SCE without acetic acid in the dark. The electrochem. C-skeleton rearrangement was postulated to proceed via formation of anionic intermediates. The electrolysis of 1-bromo-2-cyano-2-ethoxycarbonylpropane, 2-acetyl-1-bromo-2-ethoxycarbonylpropane, and 1-bromo-2-[(ethylthio)carbonyl]propane with I also afforded the corresponding skeleton rearrangement products. The results indicated that substrates with 2 electron-withdrawing groups placed on the β-carbon atom with combinations of 1 carboxylic ester and 1 of carboxylic ester, acetyl, or cyano moiety readily gave the corresponding rearrangement products which were derived from individual migration of the substituent groups. Substrates with only 1 of the electron-withdrawing groups, (carboxylic ester, acetyl, or cyano) did not give any rearrangement product, but a substrate with thioester group afforded the corresponding rearrangement product. The migratory aptitude of electron-withdrawing groups decreased in the order: COSR>COR>COOR>CN. Both electronic character and steric bulkiness of the migrating groups are apparently reflected on this tendency, even though relative contributions of these effects are much dependent on the nature of β-substituents.
Bulletin of the Chemical Society of Japan published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is C4H7BrO2, SDS of cas: 56970-78-6.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary