Synthesis of Carbene-Stabilized PNPN Fragments and Their Carbene-Dependent Redox Properties
Etienne A. LaPierre,
Brian O. Patrick,
Ian Manners
Abstract:Herein, we report the synthesis of carbene-stabilized 1,3-diaza-2,4-diphosphabutenes CAAC Me PNPNCAAC Me 4 CAAC (CAAC Me = 1-[2,6-bis(isopropyl)phenyl]-3,3,5,5-tetramethyl-2-pyrrolidinylidene) and IPrPNPNIPr 4 NHC (IPr = 1,3-Bis(2,6-diisopropylphenyl)-imidazol-2-ylidene). The bonding in both systems is defined by a delocalized polar covalent π-system, with 4 NHC exhibiting increased conjugation relative to 4 CAAC . The nature of the stabilizing carbene also influences the redox properties of the compound, with… Show more
“…1a. 24–39 This approach can result in the synthesis of highly stable organic radicals that are resistant to air and heat. In our previous research, we synthesized 1,2-dicarbonyl radical cations derived from two identical NHCs or CAACs (Fig.…”
A simplified stepwise synthesis of sterically congested unsymmetrical 1,2-dicarbonyl radicals is demonstrated. An aryl- and N-heterocyclic carbene-substituted 1,2-dicarbonyl radical is generated, revealing N-heterocyclic carbenes stabilizing role.
“…1a. 24–39 This approach can result in the synthesis of highly stable organic radicals that are resistant to air and heat. In our previous research, we synthesized 1,2-dicarbonyl radical cations derived from two identical NHCs or CAACs (Fig.…”
A simplified stepwise synthesis of sterically congested unsymmetrical 1,2-dicarbonyl radicals is demonstrated. An aryl- and N-heterocyclic carbene-substituted 1,2-dicarbonyl radical is generated, revealing N-heterocyclic carbenes stabilizing role.
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