Xiong Yongming, Ma Xue Lin, Su Shilong, Miao Qian
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.
State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.
Beilstein J Org Chem. 2025 Jan 2;21:1-7. doi: 10.3762/bjoc.21.1. eCollection 2025.
The polycyclic skeleton of tris(4,5-dehydro-2,3:6,7-dibenzotropone) is a key structural fragment in carbon schwarzites, a theoretical form of negatively curved carbon allotrope. This report presents a new synthesis of this compound using a Ni-mediated Yamamoto coupling reaction and structural analysis of it with X-ray crystallography. Interestingly, it is observed that tris(4,5-dehydro-2,3:6,7-dibenzotropone) crystallized from its solution in hexane resulting in colorless and yellow crystal polymorphs, where it adopts conformations of approximate and symmetry, respectively. Furthermore, expanding its π-skeleton through the Barton-Kellogg and Scholl reactions led to the successful synthesis of a curved polycyclic arene containing three heptagons and two pentagons.
三（4,5-脱氢-2,3:6,7-二苯并卓酮）的多环骨架是碳黑烯中的关键结构片段，碳黑烯是一种负曲率碳同素异形体的理论形式。本报告介绍了一种使用镍介导的山本偶联反应合成该化合物的新方法，并通过X射线晶体学对其进行结构分析。有趣的是，观察到三（4,5-脱氢-2,3:6,7-二苯并卓酮）从其在己烷中的溶液中结晶，形成无色和黄色晶体多晶型物，其中它分别采用近似 和 对称的构象。此外，通过巴顿-凯洛格反应和肖尔反应扩展其π骨架，成功合成了一种包含三个七边形和两个五边形的弯曲多环芳烃。
