Department of Chemistry and ‡Department of Materials Science and Engineering, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
J Org Chem. 2016 Jul 1;81(13):5595-605. doi: 10.1021/acs.joc.6b00927. Epub 2016 Jun 9.
This report describes the synthesis and characterization of a series of borepin-based polycyclic aromatics bearing two different arene fusions. The borepin synthesis features streamlined Ti-mediated alkyne reduction, leading to Z-olefins, followed by direct lithiation and borepin formation. These molecules allow for an assessment of aromatic competition between the fused rings and the central borepin core. Crystallographic, magnetic, and computational studies yielded insights about the aromaticity of novel, differentially fused [b,f]borepins and allowed for comparison to literature compounds. Multiple borepin motifs were also incorporated into polycyclic aromatics with five or six rings in the main backbone, and their properties were also evaluated.
本报告描述了一系列含有两个不同芳烃融合的基于 borepin 的多环芳烃的合成和表征。borepin 的合成特点是通过流线型的 Ti 介导的炔烃还原生成 Z-烯烃，然后直接进行锂化和 borepin 形成。这些分子允许评估融合环和中心 borepin 核之间的芳香性竞争。晶体学、磁性和计算研究提供了关于新型、不同融合的[b,f]borepins 芳香性的见解，并允许与文献化合物进行比较。多个 borepin 基元也被纳入具有主链中五个或六个环的多环芳烃中，并且还评估了它们的性质。
