META-SUBSTITUENT EFFECTS ON BENZYL FREE-RADICAL STABILITY

被引：49

作者：

FISHER, TH

DERSHEM, SM

PREWITT, ML

机构：

[1] Department of Chemistry, Mississippi State University, Mississippi State

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 03期

关键词：

D O I：

10.1021/jo00290a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 5-substituted 3-cyanotoluenes was synthesized, and the relative rates of N-bromosuccinimide bromination were determined in benzene at 80 °C. The resulting F* values of meta Me, H, Br, NO2, and CN were found to be 0.03, 0.00, -0.03, -0.04, and -0.10, respectively. Of these meta substituents, all but methyl were found to be destabilizing to the intermediate benzyl free radical. These meta substituent results are consistent with reported σa and αc: values and cast doubt upon reports that assume meta substituents have no influence on free-radical stability. © 1990, American Chemical Society. All rights reserved.

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页码：1040 / 1043

页数：4

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