Polar radicals. 15. Interpretation of substituent effects on the mechanism of electrolytic reduction of the carbon-halogen bond in series of substituted benzyl halides

…, JA Plambeck, DW Reed, TW Mojelsky

Index: Tanner, Dennis D.; Plambeck, James A.; Reed, Darwin W.; Mojelski, Thomas W. Journal of Organic Chemistry, 1980 , vol. 45, # 25 p. 5177 - 5183

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Citation Number: 37

Abstract

The electrochemical polarographic reduction of a series of substituted benzyl chlorides and benzyl bromides showed half-wave potentials which gave excellent Hammett linear free- energy correlations for each series. These correlations were obtained using u-substituent constants. The correlation with u-suggests that the potential-determining electrochemical process involves carbon-halogen bond breaking or, alternatively, radical anion ...