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Updated: Oct 1, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Monoazadichalcogenasumanenes: Synthesis, Structures, and Ring Reconstruction via Atom Transfer under Acidic
Jihai Shang1, Renjie Wang1, Chengshan Yuan1
1State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou, 730000, Gansu Province, China.
Abstract:
Buckybowls have unique properties that can be tailored by embedding main-group elements into their π-scaffolds. Herein, a synthetic approach is developed for producing monoazadichalcogenasumanenes (4 a/4 b, 6 a/6 b, 7 a/7 b) derived from sumanene by replacing its three benzylic carbons with one nitrogen and two chalcogen atoms (S for 4 a/4 b, Se for 6 a/6 b, Te for 7 a/7 b). Monoazadichalcogenasumanenes are deeper π-bowls than trichalcogensumanenes as the C-N bond is much shorter than C-X (X=S, Se, Te). The bowl-depth of 4 b (0.95 Å) is greater than that of corannulene (0.85 Å). The nitrogen atom donates electron density to the entire π-system that makes monoazadichalcogenasumanenes electron-rich. They undergo ring reconstruction of chalcogenophene ring via transferring a chalcogen atom from one molecule to another under acidic conditions. The nitrogen and chalcogen atoms play crucial role on this reaction.
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