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

Emmanuelle Despagnet-Ayoub, Karinne Miqueu, Jean-Marc Sotiropoulos, Lawrence M. Henling, Michael W. Day, Jay A. Labinger, John E. Bercaw

Research output: Contribution to journalArticlepeer-review

25 Scopus citations

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. © 2013 The Royal Society of Chemistry.
Original languageEnglish (US)
Pages (from-to)2117
JournalChemical Science
Volume4
Issue number5
DOIs
StatePublished - 2013
Externally publishedYes

Fingerprint

Dive into the research topics of 'Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene'. Together they form a unique fingerprint.

Cite this