meso-Triaryl-Substituted Smaragdyrins: Facile Aromaticity Switching
| Autor: | Atsuhiro Osuka, Mingbo Zhou, Naoki Aratani, Yutao Rao, Gakhyun Kim, Qingyun Liu, Daguan Xie, Jianxin Song, Dongho Kim, Bangshao Yin, Ling Xu, Takayuki Tanaka, Shubin Liu, Donghai Yu, Yang Liu |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Smaragdyrin Aromaticity General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry Methanesulfonic acid Catalysis 0104 chemical sciences Bimetal chemistry.chemical_compound Colloid and Surface Chemistry chemistry Nucleophilic aromatic substitution Antiaromaticity |
| Zdroj: | Journal of the American Chemical Society. 140(48) |
| ISSN: | 1520-5126 |
| Popis: | All-aza smaragdyrin, a historic but elusive pentapyrrolic macrocycle, was successfully synthesized and characterized for the first time. [22]Smaragdyrin BF2-complex 3 was smoothly synthesized by 2-fold SNAr reaction of 1,9-dibromo-5-mesityldipyrrin with 5,10-dimesityltripyrrane. Treatment of 3 with methanesulfonic acid gave [20]smaragdyrin 5 as a stable antiaromatic compound. Reduction of 5 with NaBH4 under inert conditions gave [22]smaragdyrin 6 as an aromatic congener, which was easily oxidized back to 5 in the air. Complex 3 was interconvertible with its 20π-congener 4 via oxidation with MnO2 and reduction with NaBH4. Treatment of 3 or 4 with CuCl2 in the presence of NaOAc gave hetero bimetal complex 8. |
| Databáze: | OpenAIRE |
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