Isohexide dinitriles: a versatile family of renewable platform chemicals

J. Wu, S. Thiyagarajan, C. Fonseca Guerra, P. Eduard, M. Lutz, B.A.J. Noordover, C.E. Koning, D.S. van Es

Research output: Contribution to journalArticleAcademicpeer-review

7 Citations (Scopus)

Abstract

Building blocks of isohexides extended by one carbon atom at the 2- or 5-positions are now synthetically accessible by a convenient, selective, base-catalyzed epimerization of the corresponding dinitriles. Kinetic experiments using the strong organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) show that all three possible isohexide dinitrile isomers exist within a dynamic equilibrium. An epimerization mechanism based on density functional theory (DFT) calculations is proposed. Structural identification of all three possible isomers is based on NMR analysis and single crystal x-ray crystallography. DFT calculations confirm that the observed crystal structures are indeed the lowest energy conformers of these isohexide derivatives.

Original languageEnglish
Pages (from-to)3202-3211
Number of pages10
JournalChemSusChem
Volume10
Issue number16
DOIs
Publication statusPublished - 24 Aug 2017

Keywords

  • Biomass
  • Crystal structures
  • Epimers
  • Isohexides
  • Oxygen heterocycles
  • Green Chemistry Technology
  • Nitriles/chemistry
  • Stereoisomerism
  • Molecular Conformation
  • Models, Molecular
  • Quantum Theory
  • Catalysis
  • Kinetics
  • Bridged Bicyclo Compounds, Heterocyclic/chemistry

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