ChemSusChem
ChemSusChem
5 years ago

Isohexide Dinitriles: A Versatile Family of Renewable Platform Chemicals

Isohexide Dinitriles: A Versatile Family of Renewable Platform Chemicals
Jing Wu, Bart A. J. Noordover, Daan S. van Es, Martin Lutz, Pieter Eduard, Cor E. Koning, Célia Fonseca Guerra, Shanmugam Thiyagarajan
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. As easy as ABC-DBU: 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. Density functional theory (DFT) calculations confirm that the observed crystal structures are indeed the lowest energy conformers of these isohexide derivatives.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/cssc.201700617

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