Isohexide Dinitriles: a versatile family of renewable platform chemicals
Files
Publication date
2017-08-24
Authors
Wu, Jing
Thiyagarajan, Shanmugam
Fonseca Guerra, C?lia
Eduard, Pieter
Lutz, M.
Noordover, Bart A. J.
Koning, Cor E.
Van Es, Daan S.
Editors
Advisors
Supervisors
Document Type
Article
Metadata
Show full item recordCollections
License
taverne
Abstract
New 2/5 1-carbon extended isohexide building blocks 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 are in a dynamic equilibrium. An epimerization mechanism is proposed, based on DFT calculations. Structural identification of all three possible isomers is based on NMR analysis as well as single crystal x-ray crystallography. DFT calculations confirmed that the observed crystal structures are indeed the lowest energy conformers of these isohexide derivatives.
Keywords
biomass, base-indiced epimerization, crystal structures, DFT, oxygen heterocycles, Taverne, SDG 7 - Affordable and Clean Energy
Citation
Wu, J, Thiyagarajan, S, Fonseca Guerra, C, Eduard, P, Lutz, M, Noordover, B A J, Koning, C E & Van Es, D S 2017, 'Isohexide Dinitriles: a versatile family of renewable platform chemicals', ChemSusChem, vol. 10, no. 16, pp. 3202–3211. https://doi.org/10.1002/cssc.201700617