BN-Analogues of 1,2-Didehydrobenzene: 1,2-Azaborines as reactive intermediates

1,2-二脱氢苯的 BN 类似物：1,2-氮杂硼烷作为反应中间体

• 批准号: 237455100
• 负责人: Professor Dr. Holger Bettinger
• 金额: --
• 依托单位: Institut für Organische Chemie
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2013
• 资助国家: 德国
• 起止时间: 2012-12-31 至 2021-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/237455100?language=en
• 关键词: BN; Analogues; Didehydrobenzene; Azaborines; reactive

Arynes, Didehydrobenzenes, are very versatile reactive intermediates in organic synthesis. The formal isoelectronic substitution of the CC triple bond of 1,2-didehydrobenzene (C6H4) by a boron-nitrogen (BN) unit yields 1,2-azaborine (C4BNH4). The BN-arynes have in analogy to arynes the potential to be utilized as reactive intermediates in the synthesis of novel BN-substituted compounds. BN-arynes, unknown before this research project started, could be for the first time established as reactive intermediates under matrix isolation conditions and in solution. Within this research project the reactivity of 1,2-azaborines is to be investigated comprehensively. Various methods and conditions of 1,2-azaborine generation are employed (thermal, photochemical, gas phase, noble gas matrix, organic glasses, solution) and the reactivity towards a number of trapping reagents is being studied. Furthermore, the electronic and steric stabilization of 1,2-azaborines by suitable groups is to be investigated.

芳炔类化合物，即二脱氢苯，是有机合成中用途非常广泛的反应中间体。1，2-二脱氢苯（C6 H4）的CC三键被硼-氮（BN）单元的形式等电子取代产生1，2-氮杂硼杂环（C4 BNH 4）。BN-芳炔类似于芳炔，具有在合成新的BN-取代的化合物中用作反应性中间体的潜力。BN-芳炔，未知之前，本研究项目开始，可以为第一次建立作为反应中间体在基质隔离条件下，并在解决方案。在本研究项目中，将全面研究1，2-氮杂硼杂环的反应性。采用各种方法和条件的1，2-氮杂硼代（热，光化学，气相，惰性气体基质，有机玻璃，溶液）和对一些捕获试剂的反应性正在研究中。此外，电子和空间稳定的1，2-氮杂硼杂环由合适的基团进行了研究。