EGOROV et al.
1200
2-(But-2-en-1-yl)-2H-tetrazole (5a). IR spectrum,
ν, cm–1: 3136, 2961, 2934, 2874, 1676, 1450, 1379,
1340, 1283, 1188, 1134, 1097, 1026, 1007, 966, 881,
Found, %: C 65.41; H 6.86; N 27.73. C11H14N4. Cal-
culated, %: C 65.32; H 6.98; N 27.70.
2-(Adamantan-1-yl)-2H-tetrazole (3a). The prod-
uct was recrystallized from ethanol. Yield 0.243 g
(85%), white crystalline powder. IR spectrum, ν, cm–1:
2905, 2851, 1456, 1352, 1346, 1304, 1254, 1205, 1115,
1078, 1055, 1033, 1022, 981, 927, 841, 816, 770, 694,
1
793, 706, 683. H NMR spectrum (CDCl3), δ, ppm:
1.72–1.73 m (3H), 5.15 d (2H, J = 6.8 Hz), 5.66–
5.74 m (1H), 5.84–5.93 m (1H), 8.48 s (1H). 13C NMR
spectrum (CDCl3), δC, ppm: 19.9, 54.9, 118.2, 133.3,
152.7. Found, %: C 48.50; H 6.51; N 44.99. C5H8N4.
Calculated, %: C 48.37; H 6.50; N 45.13.
1
656, 551, 521, 466, 428. H NMR spectrum (CDCl3),
δ, ppm: 1.81 m (6H), 2.29 m (3H), 2.34 m (6H), 8.48 s
(1H). 13C NMR spectrum (CDCl3), δC, ppm: 29.4, 35.8,
42.2, 64.0, 152.1. Found, %: C 64.70; H 7.92; N 27.38.
C11H16N4. Calculated, %: C 64.68; H 7.90; N 27.43.
2-(But-3-en-2-yl)-2H-tetrazole (5b). IR spectrum,
ν, cm–1: 3132, 2960, 2934, 2877, 1675, 1460, 1385,
1341, 1279, 1190, 1134, 1099, 1021, 1013, 969, 881,
1
2-(Adamantan-1-yl)-5-methyl-2H-tetrazole (3b).
The product was recrystallized from ethanol. Yield
0.244 g (80%), white crystalline powder. IR spectrum,
ν, cm–1: 2916, 2850, 1499, 1452, 1356, 1315, 1188,
1167, 1103, 1088, 1053, 1022, 983, 970, 937, 847, 816,
793, 710, 686. H NMR spectrum (CDCl3), δ, ppm:
1.75 d (3H, J = 10.0 Hz), 5.22–5.29 m (2H), 6.05–
6.14 m (1H), 5.51 quint (1H, J = 6.7 Hz), 8.49 s (1H).
13C NMR spectrum (100 MHz), δC, ppm: 17.7, 62.1,
122.6, 136.6, 152.9. Found, %: C 48.42; H 6.53;
N 45.05. C5H8N4. Calculated, %: C 48.37; H 6.50;
N 45.13.
1
771, 712, 669, 472. H NMR spectrum (CDCl3), δ,
ppm: 1.38 m (6H), 1.84 m (3H), 1.88 m (6H), 2.07 s
(3H). 13C NMR spectrum (CDCl3), δC, ppm: 10.4, 29.0,
35.5, 41.8, 62.6, 161.2. Found, %: C 66.12; H 8.25;
N 25.63. C12H18N4. Calculated, %: C 66.02; H 8.31;
N 25.67.
Hept-2-en-4-ol (6). A 250-mL three-necked flask
was charged with 5.0 g (0.206 mol) of magnesium and
a crystal of iodine. The flask was heated until violet
iodine vapor appeared and cooled to room temperature,
100 mL of anhydrous diethyl ether was added, and
about 2 g (0.016 mol) of 1-bromopropane was added
dropwise with stirring. The mixture was carefully
heated on a water bath to initiate a reaction (diethyl
ether characteristically boiled up), and 24.3 g
(0.198 mol) of 1-bromopropane was added dropwise.
The mixture was then cooled to 0–5°C, 10 g
(0.143 mol) of crotonaldehyde was added dropwise
with stirring, maintaining the temperature at 0–5°C,
and the mixture was stirred for 10 min at that tempera-
ture, poured into a mixture of 100 g of ice and 15 g of
ammonium chloride, and extracted with chloroform
(3×50 mL). The combined extracts were washed with
water and dried over anhydrous sodium sulfate, the
solvent was distilled off, and the residue was distilled.
Yield 14.0 g (86%), colorless liquid. IR spectrum, ν,
cm–1: 3345, 2959, 2934, 2874, 1674, 1452, 1441, 1377,
1309, 1217, 1177, 1143, 1121, 1067, 1011, 964, 903,
2-(Adamantan-1-yl)-5-phenyl-2H-tetrazole (3c).
The product was recrystallized from ethanol. Yield
0.314 g (80%), white crystalline powder. IR spectrum,
ν, cm–1: 2912, 2853, 1528, 1463, 1447, 1358, 1346,
1306, 1186, 1168, 1107, 1049, 1030, 926, 843, 816,
1
789, 770, 729, 702, 692, 596, 525, 507, 474. H NMR
spectrum (CDCl3), δ, ppm: 1.77 m (6H), 2.25 m (3H),
2.36 m (6H), 7.41–7.44 m (3H), 8.13–8.15 m (2H).
13C NMR spectrum (CDCl3), δC, ppm: 34.0, 40.5, 46.9,
68.5, 158.8. Found, %: C 72.84; H 7.26; N 19.90.
C17H20N4. Calculated, %: C 72.83; H 7.19; N 19.98.
2-Benzyl-2H-tetrazole (4). The reaction mixture
was heated at 55°C for 24 h, and the product was
purified by column chromatography using n-hexane–
ethyl acetate (80:20). Yield 0.103 g (46%), light yellow
oily liquid. IR spectrum, ν, cm–1: 2918, 2850, 2361,
1602, 1494, 1454, 1340, 1281, 1124, 1074, 1026, 881,
1
825, 694. H NMR spectrum (CDCl3), δ, ppm: 5.79 s
(2H), 7.39 s (5H), 8.52 s (1H). 13C NMR spectrum
(CDCl3), δC, ppm: 56.7, 128.5, 129.1, 153.3. Found, %:
C 60.06; H 5.08; N 34.86. C8H8N4. Calculated, %:
C 59.99; H 5.03; N 34.98.
1
847, 745, 507. H NMR spectrum (CDCl3), δ, ppm:
0.81 t (3H), 1.27 m (2H), 1.43 m (2H), 1.59 m (3H),
3.90 m (1H), 5.33–5.54 m (2H). 13C NMR spectrum
(CDCl3), δC, ppm: 13.8, 17.5, 18.6, 39.3, 72.5, 125.9,
134.5. Found, %: C 73.73; H 12.17. C7H14O. Calculat-
ed, %: C 73.63; H 12.36.
2-(But-2-en-1-yl)-2H-tetrazole (5a) and 2-(but-3-
en-2-yl)-2H-tetrazole (5b). The isomers were separat-
ed by column chromatography using n-hexane–butan-
1-ol (95:5) as eluent. Overall yield 0.122 g (70%), ratio
5a:5b 1.2:1, light yellow oily liquid.
2-(Hept-2-en-4-yl)-2H-tetrazole (7a) and 2-(hept-
3-en-2-yl)-2H-tetrazole (7b) were synthesized
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 7 2020