1
860
KUZNETSOV et al.
of urea, 1.41 g (22.7 mmol) of ethylene glycol, and
The products were identified by GC/MS using
an Agilent GC 7890A–MSD 5975C inert XL EI/CI in-
strument (quadrupole mass analyzer; electron impact,
70 eV). The elemental compositions were determined
on a Perkin Elmer 2400 CHN analyzer.
1
0 mL of 1,2-dichloroethane or 1,1,2,2-tetrachloro-
ethane was heated for 24 h under reflux with stirring.
When the reaction was complete, the solvent was
removed by decanting. The remaining viscous material
was a mixture of zinc(II) chloride ammonium complex
and unreacted initial compounds. It was washed with
the corresponding solvent (3×3 mL), and the washings
were combined with the decanted solution and evapo-
rated on a rotary evaporator at 50°C under reduced
pressure. Yield of ethylene carbonate 0.62 g (31%),
purity 100% (GLC). Found, %: C 40.90; H 4.59.
This study was performed under financial support
by the Government of Sverdlovsk Oblast and by the
Russian Foundation for Basic Research (project
no. 13-03-96
0
85r_ural_a).
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m/z 88 [M] . C H O . Calculated, %: C 40.92; H 4.58.
3
4
3
M 88.06.
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anhydrous zinc(II) chloride was 1.24 g (62%), purity
+
1
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and 25%, respectively. Analogous reactions were
carried out with propane-1,2-diol, propane-1,3-diol,
butane-1,3-diol, and butane-2,3-diol (see table).
Alkylene carbonates were formed most readily
from vicinal glycols, and the yield increased in parallel
with the number of substituents, which suggests an es-
sential role of steric factor in the cyclization process.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 12 2013