M. Granström et al. / Tetrahedron Letters 50 (2009) 1744–1747
1747
10. (a) Heinze, T.; Dicke, R.; Koschella, A.; Henning Kull, A.; Klohr, E-A.; Koch, W.
Macromol. Chem. Phys. 2000, 201, 627–631; (b) Goodlett, V.; Dougherty, J.;
Patton, H. J. Polym. Sci. Part A1 1971, 9, 155–160.
Supplementary data
11. In order to determine the DS by 1H NMR NMR, compound 2 was firstly
detritylated using concd HCl in THF (yield: 85%, structure was confirmed by IR)
as described for compound 1,17 and then propionylated according to Heinze
et al.10 (yield 92%, structure was confirmed by 1H NMR). The DS was then
calculated from the 1H NMR NMR spectrum as described previously by
Supplementary data associated with this article can be found, in
References and notes
Goodlett et al.10b: DS ¼ 3 ꢀ 37ꢁꢁIIPropyl
.
H;AGU
IPropyl = The integral of the chemical shift of the methyl protons of the
propionoyl substituents, IH,AGU = the integral of all the protons of
anhydroglucose unit (AGU) of cellulose.
1. Schultz, P.; Lüning, U. Macromol. Chem. Phys. 2002, 203, 961–967.
2. (a) Granström, M.; Kavakka, J.; King, A.; Majoinen, J.; Mäkelä, V.; Helaja, J.;
Hietala, S.; Virtanen, T.; Maunu, S.-L.; Argyropoulos, D. S.; Kilpeläinen, I.
Cellulose 2008, 15, 481–488; (b) Myllymäki, V.; Aksela, R. WO2005017001,
2005; Chem. Abstr. 2005, 142, 242565.; (c) Swatloski, R.; Spear, S.; Holbrey, J.;
Rogers, R. J. Am. Chem. Soc. 2002, 124, 4974–4975; (d) Schlufter, K.; Schmauder,
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8. 4-Methoxytrityl chloride (6.2 g, 20 mmol) was dissolved in pyridine (5.0 mL,
60 mmol) and was added to a solution of cellulose (1.0 g, 6.2 mmol), dissolved
in [amim]Cl (10.0 g) containing pyridine (2.5 mL, 30 mmol). The reaction
mixture was stirred at 60 °C for 6 h, followed by precipitation of the crude
product from a mixture of methanol and water (1:1). Yield: 1.1 g (27%);
DS = 1.8 (determined by 1H NMR using the propionylation method11).
9. Kern, H.; Whan Choi, S.; Wenz, G.; Heinrich, J.; Ehrhardt, L.; Mischnick, P.;
Garidel, P.; Blume, A. Carbohydr. Res. 2000, 326, 67–80.
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Interscience: New York, 1999; pp 102–105.
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17. Compound 1 (0.5 g, 0.77 mmol) was dissolved in THF (15.0 mL), and HCl
(0.6 mL, concd) was added in three portions (3 ꢁ 0.2 mL) over 24 h. The
reaction mixture was stirred at rt for 3 d, followed by work-up to give cellulose.
Yield: 0.1 g (80%).IR (cmꢀ1): Identical to
a
commercial microcrystalline
cellulose sample; 3340 (OH), 2910 (CH), 1100 (C–O).
18. Compound
1
(0.15 g, 0.23 mmol) was dissolved in CH2Cl2 (10.0 mL) and
FeCl3ꢃ6H2O (0.2 g, 7.2 ꢁ 10ꢀ4 mol) was added in one portion. The reaction
mixture was stirred at rt overnight, followed by work-up to give cellulose.
Yield: 0.04 g (100%)IR (cmꢀ1): Identical to
a commercial microcrystalline
cellulose sample; 3340 (OH), 2910 (CH), 1100 (C–O).
19. 1% I2/MeOH (2.0 mL) was added to a solution of 1 (0.14 g, 0.21 mmol) dissolved
in CH2Cl2 (10.0 mL). The reaction mixture was stirred at rt overnight, followed
by work-up to give cellulose. Yield: 0.02 g (59%).IR (cmꢀ1): Identical to a
commercial microcrystalline cellulose sample; 3340 (OH), 2910 (CH), 1100 (C–
O).
20. Wahlstrom, J.; Ronald, R. J. Org. Chem. 1998, 63, 6021–6022.
21. Schwarz, M.; Tumelty, D.; Gallop, M. J. Org. Chem. 1999, 64, 2219–2231.
22. Ding, X.; Wang, W.; Kong, F. Carbohydr. Res. 1997, 303, 445–448.