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Issue 5, 2013
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Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

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Abstract

Starting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement and a dicationic benzimidazolium-benzoxazolium salt by changing the Brønsted acid from HCl to HBF4. A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined.

Graphical abstract: Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

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Publication details

The article was received on 07 Dec 2012, accepted on 25 Feb 2013 and first published on 26 Feb 2013


Article type: Edge Article
DOI: 10.1039/C3SC22171G
Citation: Chem. Sci., 2013,4, 2117-2121

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    Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

    E. Despagnet-Ayoub, K. Miqueu, J. Sotiropoulos, L. M. Henling, M. W. Day, J. A. Labinger and J. E. Bercaw, Chem. Sci., 2013, 4, 2117
    DOI: 10.1039/C3SC22171G

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