Journal of Molecular Structure, volume 1227, pages 129427
Oximes of 3,7-dimethylocta-2,6-dienal: Green synthesis, preparative separation of all diastereomers and complete assignment of 1H and 13C NMR spectra
1
Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia.
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Publication type: Journal Article
Publication date: 2021-03-01
Journal:
Journal of Molecular Structure
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 3.8
ISSN: 00222860
Organic Chemistry
Inorganic Chemistry
Spectroscopy
Analytical Chemistry
Abstract
A mixture of four diastereomeric oximes was prepared starting from citral, an inexpensive mixture of neral and geranial ((Z)- and (E)-3,7-dimethylocta-2,6-dienal, respectively), in a solvent-free mechano-chemical reaction with NH2OH•HCl/NaOH, at room temperature. All stereoisomeric oximes ((1E,2E), (1Z,2E), (1E,2Z), and (1Z,2Z)) were isolated in pure state by isocratic silica-gel column chromatography. For the first time, the oximes were separated and individually characterized by 1D- and 2D-NMR spectroscopy in two deuterated solvents. Their spectra were fully assigned and mutually compared. Coupling constant values of higher-order multiplets belonging to the –CH2CH2- moiety were determined from (iterative) spin simulations. A careful analysis of the NOESY spectra of all diastereomers revealed that the oximes formed hydrogen-bonded adducts in CDCl3. Under the oximation conditions, the configuration of the C2-C3 double bond in the conjugated enals did not change. Prolonged standing of pure oximes of citral in either CDCl3 or DMSO‑d6 led to isomerization of the C N bond while keeping the conjugated C C bond configuration unaltered. The equilibrium ratio of the anti- to syn-oximes in solution corresponded to their ratio in the original reaction mixture. The conditions of GC were sufficient to cause dehydration of the oximes to geranyl or neryl nitriles, and/or isomerization to occur in the heated areas of the instrument, giving more complex chromatograms than expected and being dependent on the identity of the analyzed oxime.
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Radulović N., Tasić M. M., Mladenovic M. Oximes of 3,7-dimethylocta-2,6-dienal: Green synthesis, preparative separation of all diastereomers and complete assignment of 1H and 13C NMR spectra // Journal of Molecular Structure. 2021. Vol. 1227. p. 129427.
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Radulović N., Tasić M. M., Mladenovic M. Oximes of 3,7-dimethylocta-2,6-dienal: Green synthesis, preparative separation of all diastereomers and complete assignment of 1H and 13C NMR spectra // Journal of Molecular Structure. 2021. Vol. 1227. p. 129427.
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TY - JOUR
DO - 10.1016/j.molstruc.2020.129427
UR - https://doi.org/10.1016/j.molstruc.2020.129427
TI - Oximes of 3,7-dimethylocta-2,6-dienal: Green synthesis, preparative separation of all diastereomers and complete assignment of 1H and 13C NMR spectra
T2 - Journal of Molecular Structure
AU - Radulović, Niko
AU - Tasić, Magdalena M
AU - Mladenovic, Marko
PY - 2021
DA - 2021/03/01 00:00:00
PB - Elsevier
SP - 129427
VL - 1227
SN - 0022-2860
ER -
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@article{2021_Radulović,
author = {Niko Radulović and Magdalena M Tasić and Marko Mladenovic},
title = {Oximes of 3,7-dimethylocta-2,6-dienal: Green synthesis, preparative separation of all diastereomers and complete assignment of 1H and 13C NMR spectra},
journal = {Journal of Molecular Structure},
year = {2021},
volume = {1227},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.molstruc.2020.129427},
pages = {129427},
doi = {10.1016/j.molstruc.2020.129427}
}