Issue 107, 2015

Labile dioxy-functionalised zwitterionic imidazolinium salt: access to zwitterionic and neutral imidazolidin-2-ylidene derivatives and π-acceptor properties of imidazolidine-2-selones

Abstract

The dioxy-functionalised zwitterionic imidazolinium salt (3) is synthesised by the condensation of N,N′-dimesitylformamidine with glyoxal in the presence of ammonium tetrafluoroborate. The nucleophilicity of the carbene carbon is ascertained using the in situ generated anionic NHC from 3 with different electrophiles. Furthermore, 3 consists of a labile anionic five membered C2O2B at the backbone position of the imidazolinium unit, which can be tailored to prepare neutral NHC chalcogen compounds containing symmetrical and unsymmetrical oxy-functionalisation at the backbone. Furthermore, the π-acceptor properties of NHCs were evaluated using 77Se NMR in their respective imidazolidine-2-selones.

Graphical abstract: Labile dioxy-functionalised zwitterionic imidazolinium salt: access to zwitterionic and neutral imidazolidin-2-ylidene derivatives and π-acceptor properties of imidazolidine-2-selones

Supplementary files

Article information

Article type
Paper
Submitted
01 Aug 2015
Accepted
24 Sep 2015
First published
25 Sep 2015

RSC Adv., 2015,5, 87888-87896

Author version available

Labile dioxy-functionalised zwitterionic imidazolinium salt: access to zwitterionic and neutral imidazolidin-2-ylidene derivatives and π-acceptor properties of imidazolidine-2-selones

V. Gupta, V. Karthik and G. Anantharaman, RSC Adv., 2015, 5, 87888 DOI: 10.1039/C5RA15333F

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