Homolytic Aromatic Arylation

Orientation and Relative Reaction Rate Factors in Aromatic Substitution by the Benzenesulfonimido Radical

“…been found to be i ndependof the source of the radical, provided that the reactions occur at same temperature (6,68). The temperature on the other hand seems to have a fairly large effect on the final percentages of the isomers.…”

“…Organic azides have been reviewed recently by Boyer and Canter (21), and good discussions can be found in books by Sidgwick (107), and Degering (39)o Ionic aromatic substitution has been reviewed by Ingold (75), and two excellent reviews have recently appeared on homolytic aromatic substitution (6,42).…”

“…. (42), and homolytic aromatic arylation has been reviewed by Augood and Williams (6). Both reviews have expressed a definite need for a more quantitative knowledge of homolytic substitution of the aromatic nucleus.…”

“…Recently, it has been found that an electronegative substituent in the eara position of a phenyl radical gives the radical electrophilic character (6,28,65,67,87,106); it then is reasonable to assume that the proximity of the strongly electronegative sulfonyl group in the benzenesulfonimido radical also should render it electrophilic. The results of this experimentation are consistent with this hypothesis.…”

General Introduction

“…The most recent, and comprehensive reviews of different aspects of the subject have been those of Dermer and Edmison (1957) and Augood and Williams (1957).…”