OPARINA et al.
1386
196 (1) [М]+•, 152 (2), 97 (20), 96 (13), 95 (51), 94 (17),
81 (39), 70 (26), 69 (14), 68 (12), 57 (32), 55 (18), 53
(9), 52 (17), 51 (11), 45 (10), 44 (25), 43 (43), 42 (100).
of acetylene (initial pressure 14 at). The workup of the
reaction mixture was similar to that in procedure a. After
the vacuum distillation 8.62 g (88%) of the mixture of
vinyl ethers III and IV was obtained. Colorless liquid,
bp 124–126°С (8 mm Hg), nD20 1.4947. IR spectrum,
ν, cm–1: 3149 m, 3120 m, 3045 w (CH2=, CH=, Fur),
2979 s, 2923 s, 2880 s (CH2), 2767 w (cycloacetals),
1639 s, 1621 s (C=C), 1505 m (Fur), 1471 m, 1456 m,
1414 m (CH2), 1376 m, 1361 m, 1324 s (CH2=, CH=,
Fur), 1271 m (Fur), 1243 sh, 1200 s, 1154 s, 1093 s,
1058 sh, 1029 s (cycloacetals, COC, С=С), 1011 s, 983 s
(Fur), 966 s, 940 m, 924 s, 884 m, 867 m, 823 s (CH2=,
CH=, Fur), 747 s, 599 m, 534 w, 505 w (Fur). Found,
%: С 60.92; Н 5.94. C10H12O4. Calculated, %: С 61.22;
Н 6.16.
trans-5-Vinyloxy-2-(2-furyl)-1,3-dioxane (IV).
1H NMR spectrum, δ, ppm: 3.64 (2Н, Н4а,6а), 4.10 (1H,
=CHcis), 4.17 (1Н, Н5), 4.38 (2Н, Н4е,6е), 4.39 (1H,
=CHtrans), 5.49 (1Н, Н2), 6.30 (1H, =CHO), 6.36 (1Н,
Н4Fur), 6.44 (1Н, Н3Fur), 7.40 (1Н, Н5Fur). 13С NMR spec-
1
trum, δ, ppm: 66.79 (С5, JC,H 154.0 Hz), 69.03 (C4,6),
89.50 (CH2=), 95.74 (C2, 1JC,H 162.4 Hz), 107.88 (С3Fur),
110.24 (С4Fur), 142.71 (С5Fur), 149.71 (OCH=), 149.82
(С2Fur). Mass spectrum, m/z (Irel, %): 196 (2) [М]+•, 153
(1), 97 (20), 96 (14), 95 (50), 94 (17), 81 (33), 70 (34),
69 (18), 68 (9), 57 (24), 55 (20), 53 (9), 52 (12), 51 (12),
45 (13), 44 (36), 43 (45), 42 (100).
cis-4-Vinyloxymethyl-2-(2-furyl)-1,3-dioxolane
(III). 1H NMR spectrum, δ, ppm: 3.78 and 3.87 (1H
each, ОСН2), 3.99 (1Н, Н5), 4.09 (2Н, Н5, =CHcis), 4.22
(1H, =CHtrans), 4.42 (1Н, Н4), 5.90 (1Н, Н2), 6.34 (1Н,
Н4Fur), 6.47 (1H, =CHO), 6.48 (1Н, Н3Fur), 7.42 (1Н, Н5Fur).
13С NMR spectrum, δ, ppm: 67.63 (С5), 67.92 (OCH2),
74.40 (C4), 87.14 (CH2=), 98.29 (C2), 109.34 (С3Fur),
110.20 (С4Fur), 143.30 (С5Fur), 150.24 (С2Fur), 151.37
(OCH=). Mass spectrum, m/z (Irel, %): 196 (1) [М]+•, 152
(3), 139 (7), 97 (13), 96 (10), 95 (47), 94 (25), 81 (100),
69 (15), 68 (12), 57 (32), 55 (30), 53 (15), 52 (33), 51
(20), 45 (10), 44 (20), 43 (47), 42 (27).
The study was carried out under the financial support
of the program of the President of the Russian Federation
for the support of the leading scientific schools (NSh-
263.2008.3).
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107.83 (С3Fur), 110.22 (С4Fur), 142.53 (С5Fur), 149.66
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 9 2010