102 Mizuno, Nakai, and Mihara
80◦C for 5 h with vigorous stirring. After cooling
down and evacuation of carbon monoxide, copper
bromide (3.350 g, 15 mmol) was added at 20◦C un-
der air atmosphere. The reaction mixture was stirred
for additional 16 h under ambient pressure of air at
20◦C. Then, the resulting mixture was filtered (black
copper sulfide was formed), and rinsed with t-butyl
methyl ether (100 mL). After evaporation of sol-
vents and purification by short-column chromatog-
raphy (silica gel, AcOEt), glycerol carbonate (2a) was
given.
8, 8 Hz, 1H, CH2), 4.81–4.92 (m, 1H, CH); 13C NMR
(CDCl3): δ (ppm) 19.2, 70.5, 73.5, 154.9; MS m/z (%):
102 (M+, 5), 100 (11), 87 (14), 57 (100).
Stylene
carbonate
(2-oxo-4-phenyl-1,3-
dioxolane, 2d). Yield: 1.543 (94%) yield; mp
54.0◦C (Lit. [6] 56.3◦C); IR (KBr, cm−1): ν 1775
(C O), 1170, 1055, 759, 698; 1H NMR (CDCl3): δ
(ppm) 4.34 (t, J = 8 Hz, 1H, CH2), 4.80 (t, J = 8 Hz,
1H, CH2), 5.67 (t, J = 8 Hz, 1H, CH), 7.34–7.48
(m, 5H, CH); 13C NMR (CDCl3): δ (ppm) 71.1, 77.9,
125.8, 129.2, 129.7, 135.8, 154.8; MS m/z (%): 164
(M+, 100), 91 (61), 90 (91), 78 (57).
Glycerol carbonate (4-hydroxymethyl-2-oxo-1,3-
dioxolane, 2a). Yield: 1.114 g (94%) yield; oil [10]; IR
(neat, cm−1): ν 3444, 2931, 1790 (C O), 1403, 1179,
1
REFERENCES
1087; H NMR (d6-DMSO): δ (ppm) 3.46–3.53 (m,
1H, CH2), 3.62–3.69 (m, 1H, CH2), 4.27 (d,d, J = 6,
8 Hz, 1H, CH2), 4.48 (t, J = 8 Hz, 1H, CH2), 4.75–4.82
(m, 1H, CH), 5.23 (t, J = 6 Hz, 1H, OH); 13C NMR
(d6-DMSO): δ (ppm) 60.6, 65.8, 77.0, 155.1; MS (CI,
reagent gas: methane) m/z (%): 119 (M + H+, 100),
63 (4), 57 (37).
[1] Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.;
Lindner, F. Green Chem 2008, 10, 13.
[2] Rokicki, G.; Rakoczy, P.; Parzuchowski, P.; Sobiecki,
M. Green Chem 2005, 7, 529.
[3] Fukuoka, S. Chem Ind 1997, 757.
[4] Aresta, M.; Dibenedetto, A.; Nocito, F.; Pastore, C.
J Mol Catal A: Chem 2006, 257, 149.
Ethylene carbonate (2-oxo-1,3-dioxolane, 2b).
Yield: 650 mg (74%) yield; mp 35.6◦C (Lit. [6]
36.2◦C); IR (KBr, cm−1): ν 2995, 1799 (C O), 1163,
[5] Yoo, J.-W.; Mouloungui, Z. Stud Surf Sci Catal 2003,
146, 757.
[6] Mizuno, T.; Nakamura, F.; Egashira, Y.; Nishiguchi,
I.; Hirashima, T.; Ogawa, A.; Kambe, N.; Sonoda, N.
Synthesis 1989, 636.
[7] Mizuno, T.; Nakai, T.; Mihara, M. Heteroatom Chem
2009, 20, 64.
[8] Mizuno, T.; Iwai, T.; Ishino, Y. Tetrahedron 2005, 61,
9157.
[9] Mizuno, T.; Nishiguchi, I. Kagaku to Kogyo (Osaka)
1995, 69, 71; Chem Abstr 1995, 123, 8792p.
[10] Guibe, F.; Saint M’Leux, Y. Tetrahedron Lett 1981,
22, 3591.
1
1068, 773; H NMR (CDCl3): δ (ppm) 4.53 (s, 4H,
CH2); 13C NMR (CDCl3): δ (ppm) 64.5, 155.4; MS m/z
(%): 88 (M+, 100), 73 (4), 58 (13).
Propylene
carbonate
(4-methyl-2-oxo-1,3-
dioxolane, 2c). Yield: 752 mg (74%) yield; oil [6]; IR
(neat, cm−1): ν 2987, 1791 (C O), 1389, 1184, 1053;
1H NMR (CDCl3): δ (ppm) 1.50 (d, J = 6 Hz, 3H,
CH3), 4.03 (d,d, J = 8, 8 Hz, 1H, CH2), 4.56 (d,d, J =
Heteroatom Chemistry DOI 10.1002/hc