Abstract
Abstract The organocobalamin with methylitaconic acid attached to cobalt via its methyl group has been synthesized for the first time. This compound is believed to be an intermediate in the interconversion of methylitaconic acid and α-methyleneglutaric acid, catalysed by the coenzyme B12-dependent α-methyleneglutarate mutase enzyme. Reactions of this organocobalamin and the corresponding dimethyl ester demonstrate that cleavage of the Co-C bond leads to the rearranged α-methyleneglutarate structure under conditions where intermediate carbanions are formed.
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