Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
Angew Chem Int Ed Engl. 2017 Dec 4;56(49):15560-15564. doi: 10.1002/anie.201707087. Epub 2017 Nov 13.
In the long history of corannulene chemistry, the 1,3-dipolar cycloaddition to corannulene is unprecedented. Reported herein is the 1,3-dipolar cycloaddition of a polycyclic aromatic azomethine ylide to corannulene, a reaction which occurs exclusively at the rim bond of corannulene, from the convex side in an exo fashion. The cycloadducts were successfully converted, by successive oxidative dehydrogenation, into pyrrole-fused corannulenes, which exhibited pronounced solvatofluorochromism.
在冠状烯化学的悠久历史中，冠状烯的 1,3-偶极环加成反应是前所未有的。本文报道了多环芳基亚甲基叶立德与冠状烯的 1,3-偶极环加成反应，该反应仅在冠状烯的边缘键上发生，从凸面以反式方式进行。通过连续氧化脱氢，成功地将环加成产物转化为吡咯稠合的冠状烯，它们表现出明显的溶剂致变色。
