High temperature bromination. Part 12: Bromination of 7-oxabenzonorbornadiene: Synthesis of 2,3-dibromo-7-oxabenzonorbornadiene

被引：42

作者：

Altundas, A

Dastan, A

McKee, MM ^{[2
]}

Balci, M

机构：

[1] Ataturk Univ, Dept Chem, TR-25240 Erzurum, Turkey

[2] Auburn Univ, Dept Chem, Auburn, AL 36849 USA

[3] Middle E Tech Univ, Dept Chem, TR-65031 Ankara, Turkey

来源：

TETRAHEDRON | 2000年 / 56卷 / 33期

关键词：

bromination; tribromides; 7-oxabenzonorbornadiene; high temperature bromination;

D O I：

10.1016/S0040-4020(00)00561-5

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 7-oxabenzonorbornadiene (8) at 0 degrees C led in high yield to the formation of dibromoaldehyde 10. However, high-temperature bromination of 8 in carbontetrachloride at 77 degrees C gave non-rearranged products 17 and 18. From the elimination of non-rearranged products, 2-bromo-7-oxabenzonorbornadiene (12) was obtained. Similarly, bromination of monobromide 12 at 77 degrees C yielded the non-rearranged tribromides 19 and 20 while bromination of 12 at 0 degrees C gave the rearranged product 11. The dehydrobromination of tribromides (19, 20) provided the 2,3-dibromo-7-oxabenzonorbornadiene (21), which is a synthon for the trimerization, in high yield (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6115 / 6120

页数：6

共 19 条

[1] Synthesis of 2,3-dibromobenzonorbornadiene and its cyclotrimerization into 5,18:6,11:12,17-trimethanotrinaphthylene [J].