The Bromination and Mercuration of bis-Dimethylglyoxymato(alkyl)pyridinecobalt(III), Alkyl Cobaloxime

Abstract

Abstract The bromination and mercuration of cis-2-methoxycyclohexyl(pyridine)cobaloxime (I) gave trans-1-bromo-2-methoxycyclohexane (V) and trans-2-methoxycyclohexylmercury(II) chloride (VII), along with other byproducts derived from the cyclohexene formed by β-elimination. β-Elimination is an exclusive degradation path with trans-2-hydroxycyclohexyl(pyridine)cobaloxime(II). The reaction of cis and trans-4-t-butylcyclohexyl(pyridine)cobaloximes (III and IV) gave trans and cis-1-bromo-4-t-butylcyclohexanes (X and XI), and trans and cis-4-t-butylcyclohexylmercury(II) chloride, with an exculsive or preferential inversion at the reaction center. These results show that the SE2 reaction of alkyl cobaloxime takes a stereochemical course of inversion.