Cyclic carbonates
Russ. Chem. Bull., Int. Ed., Vol. 69, No. 12, December, 2020
2347
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Experimental
Commercially available macroporous sorbent Purolite A103
resin (0.6—0.85 mm bead size) containing dimethylamino-
methyl groups was washed with MeOH before use and dried for
30 min in a drying oven at 105 С. 7-Oxabicyclo[4.1.0]heptane
(1), 2-methyloxirane (3a), 2-(chloromethyl)oxirane (3b), 2-(phen-
oxymethyl)oxirane (3f), 2-phenyloxirane (3i), 2,2´-[4,4´-(prop-
ane-2,2-diyl)bis(4,1-phenylene)]bis(oxy)bis(methylene)dioxi-
rane (5) are commercially available compounds (Sigma—Aldrich).
2-(Fluoromethyl)oxirane (3c), 2-(2,2,2-trifluoroethyl)oxirane
(3d), 2-(pentafluorophenylmethyl)oxirane (3e), N,N-diethyl-2-
oxiranemethaneamine (3g), 4-(oxiran-2-ylmethyl)piperidine
(3h) were obtained according to the known procedures.32—36
Preparation of catalysts. 2-Chloroethanol (mL) was added
to the sorbent Purolite A103 resin (4 g) and heated under reflux
for 1 h. An excess of 2-chloroethanol was removed by filtration,
the polymer was washed with acetone (2×10 mL) and dried for
30 min at 105 С. Found (PS-Cl): С, 61.18; Н 8.36; N, 4.97;
Cl, 14.00. The resulting resin (2 g) was loaded in a 5 cm3 glass
column, treated with 5% aqueous NaBr solution (1.5 L) during
12 h by a slow dropwise addition and then washed with water
(0.5 L). The resulting polymeric bromide (PS-Br) was dried for
1 h at 105 С. Found: С, 55.54; Н, 7.34; N, 4.54; Br, 24.25.
Catalytic reactions. A 10 mL autoclave was charged with the
catalyst (0.05 g) and the corresponding epoxide (3 mmol) at
~20 °C; to the vessel CO2 was introduced (7, 20 or 56 atm). The
autoclave was heated to a desired temperature (see Table 1) and
the processes were carried out for 24 h without stirring. The
reactor was cooled to ~20 C, CO2 was decompressed, the resi-
due was analyzed by NMR. Spectral characteristics of carbonates
2, 4a—i, 6 were consistent with the literature data.15,30,34,37—40
Typical procedure of recycling the catalyst using cyclohexene
oxide. After the completion of the reaction (see the above pro-
cedure), CH2Cl2 (1 mL) was added to the reaction mixture, and
the catalyst was filtered. The catalyst was additionally washed
with CH2Cl2 (3×1 mL), dried on the Schott filter, and reused in
the subsequent catalytic experiment. The solvent was evapo-
rated; the conversion of compound 1 was monitored by NMR.
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This study was financially supported by the Russian
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