Disclosing Cyclic(Alkyl)(Amino)Carbenes as a One-Electron Reductant: Synthesis of Acyclic(Amino)(Aryl)Carbene-Based Kekulé Diradicaloids
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Date
2023
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Access Rights
info:eu-repo/semantics/openAccess
Abstract
Herein we disclose cyclic(alkyl)(amino)carbenes (CAACs) as a one-electron reductant under the formation of a transient radical cation as indicated by EPR spectroscopy. Subsequently, the disclosed CAAC reducing reactivity was utilized for the synthesis of acyclic(amino)(aryl)carbene-based Thiele and Chichibabin hydrocarbons, a new class of Kekulé diradicaloids. The results demonstrate the CAAC to be a potent organic reductant. Notably, the acyclic(amino)(aryl)carbene-based Chichibabin's hydrocarbon shows an appreciable population of the triplet state at room temperature, as evidenced by both variable temperature NMR and EPR spectroscopy.
Description
Keywords
EPR Spectroscopy, Reductant, Carbene, Electrochemistry, Radical Cation
Journal or Series
Chemistry
WoS Q Value
Q2
Scopus Q Value
N/A
Volume
-
Issue
-
