An equilibrium halogen transfer reaction with evidence for S(RN)1-like behavior

Article abstract of DOI:10.1021/jo00080a005

The 'reduction' of 2-chloro-6-(trichloromethyl)pyridine to the dichloromethyl derivative by chloroform under basic conditions yields carbon tetrachloride as a companion product. The reaction is demonstrated to be reversible and to have preparative value. Strong inhibition by electron capture agents and also strong acceleration by electron-donating agents is observed. The mechanistic interpretation is electron-transfer initiation followed by reversible radical chains to establish the equilibrium.