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

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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.