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一种反芳香性9-羟基芴阳离子的分离

Isolation of an Antiaromatic 9-Hydroxy Fluorenyl Cation.

作者信息

Duvinage Daniel, Mebs Stefan, Beckmann Jens

机构信息

Institut für Anorganische Chemie und Kristallographie, Universität Bremen, Leobener Straße 7, 28359, Bremen, Germany.

Institut für Experimentalphysik, Freie Universität Berlin, Arnimallee 14, 14195, Berlin, Germany.

出版信息

Chemistry. 2021 Jun 1;27(31):8105-8109. doi: 10.1002/chem.202100786. Epub 2021 May 6.

DOI:10.1002/chem.202100786
PMID:33835609
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8252458/
Abstract

Fluorenyl cations are textbook examples of 4π electron antiaromatic five-membered ring systems. So far, they were reported only as short-lived intermediates generated under superacidic conditions or by flash photolysis. Attempts to prepare a m-terphenyl acylium cation by fluoride abstraction from a benzoyl fluoride gave rise to an isolable 9-hydroxy fluorenyl cation that formed by an intramolecular electrophilic attack at a flanking mesityl group prior to a 1,2-methyl shift and proton transfer to oxygen.

摘要

芴阳离子是4π电子反芳香性五元环体系的典型例子。到目前为止，它们仅作为在超酸性条件下或通过闪光光解产生的短寿命中间体被报道。尝试通过从苯甲酰氟中夺取氟来制备间三联苯酰鎓阳离子，得到了一种可分离的9-羟基芴阳离子，它是在1,2-甲基迁移和质子转移到氧之前，通过对邻位均三甲苯基的分子内亲电攻击而形成的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/71843dedec85/CHEM-27-8105-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/fd99ef7fdfac/CHEM-27-8105-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/4f78ae8b5d40/CHEM-27-8105-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/8eac3edfd852/CHEM-27-8105-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/200f29655136/CHEM-27-8105-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/71843dedec85/CHEM-27-8105-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/fd99ef7fdfac/CHEM-27-8105-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/4f78ae8b5d40/CHEM-27-8105-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/8eac3edfd852/CHEM-27-8105-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/200f29655136/CHEM-27-8105-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3901/8252458/71843dedec85/CHEM-27-8105-g006.jpg

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本文引用的文献

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