Carbon-oxygen bond cleavage reactions by electron transfer. 2. Electrochemical formation and dimerization reaction pathways of cyanodiphenyl ether radical anions

MD Koppang, NF Woolsey…

Index: Koppang,M.D.; Woolsey,N.F.; Bartak,D.E. Journal of the American Chemical Society, 1985 , vol. 107, p. 4692

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Citation Number: 19

Abstract

Abstract: The radical anions of 4-cyanodiphenyl ether (1) and 2-cyanodiphenyl ether (2) have been electrochemically generated and subsequently shown to dimerize in dry N, N- dimethylformamide (DMF). The radical anion of 1 undergoes irreversible dimerization (k2= 1.1 X 10, MI SI) to form dimeric dianions, which result from coupling either at the 2 and 4 positions or at the 4 and 4 positions with respect to the cyano substituent. The 4-4 coupled ...