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通过汉茨施型环化反应构建吡啶稠合双(正氮杂茂):芳香桥增强反芳香性。

Pyridine-Fused Bis(Norcorrole) through Hantzsch-Type Cyclization: Enhancement of Antiaromaticity by an Aromatic Bridge.

机构信息

Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, China.

Department of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50 383, Wrocław, Poland.

出版信息

Angew Chem Int Ed Engl. 2017 Aug 28;56(36):10810-10814. doi: 10.1002/anie.201705715. Epub 2017 Jul 31.

DOI:10.1002/anie.201705715
PMID:28685991
Abstract

A non-catalytic condensation of Ni β-aminonorcorrole with aryl aldehydes is shown to produce a family of pyrromethane dimers that undergo deaminative cyclization to yield pyridine-fused bis(norcorrole)s comprising two antiaromatic macrocycles communicating by an aromatic moiety. The new compounds were characterized by spectroscopic, structural, and electrochemical methods supported by DFT calculations, all of which revealed unexpected antiaromaticity enhancement in the fused system.

摘要

镍β-氨基诺咯啉与芳醛的非催化缩合反应生成了一系列吡咯并甲烷二聚体,这些二聚体经历脱氨环化反应,生成由两个通过芳香部分连通的反芳香大环组成的吡啶稠合双(诺咯啉)。新化合物通过光谱、结构和电化学方法进行了表征,并得到了 DFT 计算的支持,所有这些方法都揭示了稠合体系中意想不到的反芳香性增强。

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