SYNTHESIS OF C-SUBSTITUTED 2,5-DIHYDRO-1H-BOROLES (3-BOROLENES)

被引：11

作者：

HERBERICH, GE

MARX, HW

WAGNER, T

机构：

[1] Institut für Anorganische Chemie, Technische Hochschule Aachen, Aachen

来源：

CHEMISCHE BERICHTE | 1994年 / 127卷 / 11期

关键词：

1H-BOROLES, 2,5-DIHYDRO; 3-BOROLENES; 2-BORAINDAN, 4,5,6,7-TETRAHYDRO;

D O I：

10.1002/cber.1491271108

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Magnesium-diene addition compounds derived from isoprene, 2,3-dimethylbutadiene, and 1,2-dimethylenecyclohexane are treated with boron halides BCl2(NR2) (R = Me, Et, iPr), PhBCl2, or MeBBr2 to give C-substituted 2,5-dihydro-1H-boroles (3-borolenes) 3-5. In a new in situ procedure 1,3-pentadiene reacts with Mg/BCl2(NR2) in THF to yield 2-methyl derivatives 2-MeC4H5BNR2 (2). The NMe3 adduct of 4,5,6,7-tetrahydro-2-methyl-2-boraindan 5e . NMe3 undergoes a topomerization with DELTAG not-equal 290 = 59 +/- 2 kJ/mol in a dissociative-associative process. The crystal structure of 3,4-dimethyl-1-phenyl-3-borolene (4d) has been determined. The molecule displays a classical planar structure. There are no indications for specific intermolecular interactions.

引用

页码：2135 / 2140

页数：6

共 55 条

[11]

Bonnemann H., 1983, ANGEW CHEM, V95, P749

[12] 2,5-DIHYDROBOROLES AND 1,3-DIHYDRO-1,3-DIBORETES FROM 1,3-DIENES AND ALKYNES FROM REACTIONS WITH DICHLORO(DIISOPROPYLAMINO)BORANE AND ALKALINE-METALS [J].