HIGH-TEMPERATURE BROMINATION .5. FUNCTIONALIZATION OF BENZONORBORNADIENE - HIGH-TEMPERATURE BROMINATION AND ELECTROCHEMICAL OXIDATION

被引：67

作者：

DASTAN, A ^{[1
]}

DEMIR, U ^{[1
]}

BALCI, M ^{[1
]}

机构：

[1] ATATURK UNIV,DEPT CHEM,ERZURUM 25240,TURKEY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 22期

关键词：

D O I：

10.1021/jo00101a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrophilic addition of bromine to benzonorbornadiene (1) at 10 degrees C led in high yield to the formation of 2-exo-7-anti-dibromide 2. However, high-temperature bromination in decalin at 150 degrees C resulted in the formation of five products, 2-6, consisting of non-rearranged and rearranged products in a ratio of 8:2. Conducting the bromination reaction in the presence of a free radical inhibitor like 2,4,6-tri-tert-butylphenol suppressed the formation of the non-rearranged products. This very strongly supports the assumption that there is a competition between radical and ionic reactions. Anodic oxidation of benzonorbornadiene was investigated. Electrolysis of benzonorbornadiene in different solvents resulted in the formation of 2,7-disubstituted benzonorborn-5-ene derivatives, 8-11, in good yields.

引用

页码：6534 / 6538

页数：5

共 19 条

[1] HIGHLY FUNCTIONALIZED BENZOBARRELENE DERIVATIVES - BROMINATION OF 2-BROMO-5,6-BENZOBICYCLO[2.2.2]OCTA-2,6-DIENE - HIGH-TEMPERATURE BROMINATION .3. [J].