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.

Arynes，Didehydrobenzenes是有机合成中非常通用的反应性中间体。由硼氮（BN）单位的1,2-二氢苯（C6H4）的CC三键形式的等递三键产生1,2-偶像杂碱（C4BNH4）。 BN-Arynes类似于Arynes，在合成新型BN取代化合物的合成中被用作反应性中间体的潜力。在该研究项目开始之前未知的BN-Arynes可能是在基质隔离条件和溶液中首次确定为反应性中间体。在该研究项目中，应全面研究1,2-氮杂线的反应性。采用了1,2-氮杂氨酸生成的各种方法和条件（热，光化学，气相，贵重气体基质，有机玻璃，溶液），并研究了对许多诱捕试剂的反应性。此外，要研究合适的组对1,2-氮杂素的电子和空间稳定。