Aryl chlorides, redox potentials

TABLE 12.1 Redox Potentials for Alkyl Halides (RX) and Aryl Chlorides (ArClx) in Dimethyl Formamide at a Glassy-Carbon Electrode"... 

W. A. Waters (Oxford University) Investigations of the extent to which complexes such as (CuCl)+ and undissociated CuCL affect the chain length in the polymerization associated with the Sandmeyer reaction are in progress at Oxford. It is well known that ions that complex well with cupric, e.g., (CN) , can be introduced into aryl nuclei by the Sandmeyer procedure in preference to chloride even when diazonium chlorides have initially been taken. The system, however, is complicated by the fact that the complexing of cuprous and cupric salts alters the redox potential, and this affects the facility of both stages 1 and 3 of the reaction sequence. The effects of introducing polar substituents into the aryl nuclei (Table I) indicates the importance of such effects. 

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