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

芳烃、二脱氢苯是有机合成中用途非常广泛的活性中间体。1，2-二脱氢苯(C6H4)的CC三键被一个硼-氮(BN)单元正式等电子取代，生成1，2-氮硼(C4BNH4)。与芳炔类似，BN-芳烃具有在合成新型BN-取代化合物中用作活性中间体的潜力。在本研究项目开始之前未知的BN-芳烃，可能首次在基质分离条件下和在溶液中被确定为活性中间体。在这项研究项目中，将全面考察1，2-氮杂硼的反应性。采用了不同的方法和条件(热法、光化学法、气相、惰性气体基质、有机玻璃、溶液)生成1，2-氮硼烷，并正在研究其对多种捕捉剂的反应性。此外，还需要研究合适基团对1，2-氮硼化合物的电子和空间稳定作用。

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.