Synthesis of Planar meso-Aryl Rosarins: A Reversible Antiaromatic/Aromatic Interconversion

Novel 24π antiaromatic and 26π aromatic meso-aryl rosarins were successfully obtained for the first time from β-free bipyrrole through a one-pot synthesis. Because of the absence of substituents at the β-positions of the pyrrole units, the β-free pristine rosarin backbones were highly planar, as con...

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Veröffentlicht in:Organic letters 2022-05, Vol.24 (20), p.3609-3613
Hauptverfasser: Liu, Ningchao, Morimoto, Hirofumi, Wu, Fan, Lv, Xiaojuan, Xiao, Bentian, Kuzuhara, Daiki, Pan, Jianming, Qiu, Fengxian, Aratani, Naoki, Shen, Zhen, Yamada, Hiroko, Xue, Songlin
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Sprache:eng
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Zusammenfassung:Novel 24π antiaromatic and 26π aromatic meso-aryl rosarins were successfully obtained for the first time from β-free bipyrrole through a one-pot synthesis. Because of the absence of substituents at the β-positions of the pyrrole units, the β-free pristine rosarin backbones were highly planar, as confirmed using X-ray crystallography. Optical measurements indicated interconversion between 24π antiaromatic and 26π aromatic β-free pristine rosarin via redox reactions, which was not observed in distorted β-dodecamethyl rosarin.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01147