Title:
Isolation of an Antiaromatic 9-Hydroxy Fluorenyl Cation
Author(s):
Duvinage, Daniel; Mebs, Stefan; Beckmann, Jens
Year of publication:
2021
Available Date:
2021-08-04T07:04:06Z
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.
Part of Identifier:
e-ISSN (online): 1521-3765
Keywords:
acylium ion
antiaromaticity
carbocation
electrophilic substitution
fluorenyl ion
DDC-Classification:
540 Chemie und zugeordnete Wissenschaften
Publication Type:
Wissenschaftlicher Artikel
URL of the Original Publication:
DOI of the Original Publication:
Journaltitle:
Chemistry - A European Journal
Department/institution:
Physik
Institut für Experimentalphysik