· supplementary information synthesis of coenzyme q0 through divanadium-catalyzed oxidation of...
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Supplementary InformationSynthesis of coenzyme Q0 through divanadium-catalyzed oxidation of 3,4,5-
trimethoxytoluene with hydrogen peroxide
Olga V. Zalomaeva,a Vasilii Yu. Evtushok,ab Gennadii M. Maksimov,a Raisa I. Maksimovskayaa and Oxana A. Kholdeeva*ab
a Boreskov Institute of Catalysis, Pr. Ac. Lavrentieva 5, Novosibirsk 630090, Russia. E-mail: [email protected]; Fax: +7-383-330-9573; Tel: +7-383-326-9433.b Novosibirsk State University, Pirogova str. 2, Novosibirsk 630090, Russia.
Table of contents
Figure S1. FTIR spectra of (Bu4N)3.5H1.5[γ-PW10V2O40]: initial and after catalytic reaction.
Figure S2. 51V NMR (400 MHz; 25 °C) spectrum of (Bu4N)3.3H1.7[γ-PW10V2O40] in dry CH3CN.
Figure S3. Potentiometric titration of (Bu4N)3.5H1.5[γ-PW10V2O40] with TBAOH.
Figure S4. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,3-dimethoxy-5-methyl-1,4-benzoquinone in CDCl3.
Figures S5-S9. 1H NMR spectra of other quinone products.
Electronic Supplementary Material (ESI) for Dalton Transactions.This journal is © The Royal Society of Chemistry 2017
1200 1000 800 600 400
after reaction
Wavenumber, cm-1
489
1039
1062
1150
704
1094
806
533
752
875
953
974
initial
Figure S1. FTIR spectra of (Bu4N)3.5H1.5[γ-PW10V2O40]: initial and after catalytic reaction.
- 579
- 581
- 5 80 - 5 85 - 5 75 ppm
Figure S2. 51V NMR (400 MHz; 0.0015 M, 25 °C) spectrum of (Bu4N)3.3H1.7[γ-PW10V2O40] in dry CH3CN.
0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.6 1.8 2.0-600-500-400-300-200-100
0100200300400500
Pote
ntia
l, m
V
TBAOH, equiv
Figure S3. Potentiometric titration of (Bu4N)3.5H1.5[γ-PW10V2O40] with TBAOH.
Figure S4. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,3-dimethoxy-5-methyl-1,4-benzoquinone in CDCl3.
Figure S5. 1H NMR (400 MHz; 25 °C) spectrum of 2-methoxy-5-methyl-1,4-benzoquinone in reaction mixture (CD3CN) after complete conversion of substrate.
Figure S6. 1H NMR (400 MHz; 25 °C) spectrum of 2-methoxy-6-methyl-1,4-benzoquinone in reaction mixture (CD3CN) after complete conversion of substrate.
Figure S7. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,6-dimethoxy-3-methyl-1,4-benzoquinone in CDCl3.
Figure S8. 1H NMR (400 MHz; 25 °C) spectrum of 2,3-dimethoxy-1,4-benzoquinone in reaction mixture (CH3CN) after complete conversion of substrate.
Figure S9. 1H NMR (400 MHz; 25 °C) spectrum of isolated 2,6-dimethoxy-1,4-benzoquinone in CDCl3