Sterically demanding bi- and tridentate alkoxy-N-heterocyclic carbenes

Polly L. Arnold, Claire Wilson

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

In contrast to the one-pot, two step syntheses we recently reported for a large number of substituted bidentate alkoxy-carbene ligands derived from epoxides, the reaction of imidazole with 2-adamantyl epoxide readily affords the bis(ethoxyadamantyl) substituted imidazolium salt [1-C{(NR)CHCH(NRH)}] (RH = CH2(2-adamantyl)OH), which has been isolated and structurally characterised as its iodide salt, [HC{(NRH)CH}(2)]I. Treatment with group 1 bases results in the loss of one ethoxy arm, to afford the structurally characterised monosubstituted alcohol imidazole, [HC{(NR)CHCHN}], or the lithium carbene complex [LiC{(NR)CHCHN}], a carbene complex containing a singly-N-functionalised alkoxy carbene. Alternatively, the monosubstituted alcohol imidazole may ben requaternised at the nitrogen atom with iso-propyl iodide to form [HC{(NRH)CHCH(NPri)}]I, from which a more standard lithium alkoxycarbene complex [LiC{(NR)CHCHNPri}] may be generated. (c) 2006 Elsevier B.V. All rights reserved.

Original languageEnglish
Pages (from-to)190-196
Number of pages7
JournalInorganica Chimica Acta
Volume360
Issue number1
DOIs
Publication statusPublished - 1 Jan 2007

Keywords / Materials (for Non-textual outputs)

  • heterocyclic carbene lithium N-ligand alkoxide imidazolium imidazole
  • CATALYZED CONJUGATE ADDITION
  • NHC LIGANDS
  • COMPLEXES
  • POLYMERIZATION
  • COPPER
  • REACTIVITY

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