AROMATIC SIDE-CHAIN BROMINATION BY N-BROMOSUCCINIC IMIDE .5. RING SUBSTITUENTS AND SELECTIVITY

被引：18

作者：

OFFERMANN, W ^{[1
]}

VOGTLE, F ^{[1
]}

机构：

[1] UNIV BONN,INST ORGAN CHEM & BIOCHEM,D-5300 BONN 1,FED REP GER

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 05期

关键词：

D O I：

10.1021/jo01319a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The selectivity (monobromination/dibromination) of N-bromosuccinic imide (NBS) toward 15 meta- and parasubstituted toluenes was evaluated by 1HNMR integration. Except for two substrates, selectivity and hence maximum yield correlate with Hammett σ+ parameters. The Hammett ρ value of the reaction XC6H4CH2Br →XC6H4CHBr2 (dibromination) is -0.88. The results demonstrate that in NBS side chain bromination substrate reactivity parallels selectivity. © 1979, American Chemical Society. All rights reserved.

引用

页码：710 / 713

页数：4

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