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吡咯并薁并氮杂蒄的合成与氧化还原性质

Synthesis and Redox Properties of Pyrrole- and Azulene-Fused Azacoronene.

作者信息

Sasaki Yoshiki, Takase Masayoshi, Okujima Tetsuo, Mori Shigeki, Uno Hidemitsu

机构信息

Graduate School of Science and Engineering , Ehime University , Matsuyama 790-8577 , Japan.

Advanced Research Support Center , Ehime University , Matsuyama 790-8577 , Japan.

出版信息

Org Lett. 2019 Mar 15;21(6):1900-1903. doi: 10.1021/acs.orglett.9b00515. Epub 2019 Mar 5.

DOI:10.1021/acs.orglett.9b00515
PMID:30835482
Abstract

Synthesis of an azacoronene, in which both pyrrole and azulene moieties are circularly fused, was achieved just in three steps. This new azacoronene exhibited multistep reversible oxidations under electrochemical and chemical conditions. Formation of an aromatic 22π-electron conjugation and a tropylium cation (6π-electron conjugation) in the dicationic state was revealed by the single-crystal X-ray crystallographic analysis as well as the nucleus-independent chemical shift (NICS) and anisotropy of the induced current density (ACID) calculations.

摘要

仅通过三步就实现了一种氮杂蒄的合成,其中吡咯和薁部分均呈环状稠合。这种新型氮杂蒄在电化学和化学条件下表现出多步可逆氧化。单晶X射线晶体学分析以及核独立化学位移(NICS)和感应电流密度各向异性(ACID)计算表明,其二价阳离子状态下形成了芳香性的22π电子共轭和环庚三烯正离子(6π电子共轭)。

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