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有机化学
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有机化学 ›› 1996, Vol. 16 ›› Issue (2): 139-144. 上一篇    下一篇

研究论文

联萘双金属化合物对胺基氯硼烷类的单转烃化反应及2-联萘基硼化合物的合成

袁国正;桂国球   

  1. 武汉大学化学系
  • 发布日期:1996-04-25

Single site transarylation of 2, 2'-dimetallized 1, 1'-binaphthyl to aminochloroboranes, synthesis of 2-binaphthyl boron compounds

YUAN GUOZHENG;GUI GUOQIU   

  • Published:1996-04-25

被引次数

3

一类新反应现象被描述。2, 2'-二锂联萘或2, 2'-双格氏化联萘当与Et2NBCl2及Et2NB(Ph)Cl反应时, 仅以一个M-C键参与亲核烃化, 另一M-C键因可能的七员环过渡态而失活。反应分别给出仅在联萘2-位取代的硼化合物Ⅱ或Ⅳ, 而得不到2, 2'-双位取代的硼化合物Ⅰ或Ⅲ。五个新硼化合物被合成, 并讨论了反应机理。

关键词: 联萘 P, 反应机理, 红外分光光度法, 硼烷类, 质谱法, 硼化合物

Reaction of 2, 2'-dilithio (or dibromomagnesio)-1, 1'-binaphthyl with 2 eqiv. of (N, N-diethylamino) phenylchloroborane, or quimolar amounts of diethylaminodichloroborane, followed by hydrolysis and chelati on with N, O-bidentate ligands, afforded the unexpected (2- binaphthyl) phenylboron chelates Ⅱ or bis (2-binaphthyl) boron chelates Ⅳ respectively, instead of the expected 1, 1'-binaphtyl- 2, 2'-bis (phenylboryl) chelates Ⅰ or dinaphthoborole derivatives Ⅲ. These evidences show that the only one M-C bond in 2, 2'-dimetallized 1, 1'-binaphthyl participates in the nucleophilic reaction with aminochloroboranes and another M-C bond loses its transarylation activity. The reaction mechanism in connection with a possible 7- membered ring transition state was describedion.

Key words: INFRARED SPECTROPHOTOMETRY, BINAPHTHYL P, MASS SPECTROGRAPHY, BORANES, BORON COMPOUNDS, REACTION MECHANISM

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