630
MAMEDOV, RASULOVA
1
H NMR spectrum, δ, ppm: 1.0–1.41 d (8H, 4CH ), 2.20–
80°C. We isolated 76.8 g (65%) of compound XIV, bp
2
20
20
2
6
.22 m (2H, 2CH), 4.6 d (1H, CH), 5.75 t (2H, CH =),
192–193°C (30 mm Hg), d 0.9678, n 1.4867. Found,
2
4 D
13
.23 d (1H, CH=). C NMR spectrum, δ, ppm: 28.08
%: C 76.22; H 10.11. C H O . Calculated, %: C 76.27;
15 24 2
H 10.16.
5
7
6
4
3
(
(
C ), 29.6 (C ), 35.45 (C ), 35.92 (C ), 40.0 (C ), 42.12
C ), 77.31 (C ), 135.6 (C ), 137.0 (C ), 168.6 (C ).
1
2
10
9
8
exo-Tricyclo[5.2.1.02,6]dec-3-en-8(9)-exo-yl
Found, %: C 72.22; H 8.80. C H O . Calculated, %: C
10
14
2
acrylate (XVI). From 66 g of compound XV, 36.0 g of
acrylic acid, and 0.18 g of the catalysts at 80°C we
obtained 83.6 g (82%) of compound XVI, bp 105–108°C
7
2.26; H 8.89.
exo-5-Methylbicyclo[2.2.1]hept-2-exo-yl acrylate
IX).Amixture of 54 g of compound II, 43.2 g of acrylic
(2 mm Hg), d 1.0882, n 1.5025. IR spectrum, ν, cm–
2
0
20
(
4 D
1
acid, and 0.22 g of the catalyst was heated at 80°C. We
isolated 68.9 g (77%) of compound IX, bp 117–118°C
: 1730 (C=O), 1300–1050 (C–O–C), 1640 (–CH=CH–
1
), 810–890 (CH =CH–). H NMR spectrum, δ, ppm: 1.32
2
2
0
20
1
(
30 mm Hg), d 0.9968, n 1.4769. H NMR spectrum,
m (2H, CH ), 1.32–2.14 m (4H, 2CH ), 2.16 d (2H, 2CH),
4
D
2 2
δ, ppm: 1.1 t (3H, CH ), 1.10–1.44 d (6H, 3CH ), 2.20–
2.46 d (2H, 2CH), 4.65 d (1H, CH), 5.55–5.60 q (2H,
3
2
13
2
.22 m (2H 2CH), 4.5–4.6 d (2H, 2CH), 5.75 t (2H,
2CH=), 5.75 t (2H, CH =), 6.23 d (1H, CH=). C NMR
2
1
3
11
12
13
CH =), 6.23 d (1H, CH=). C NMR spectrum, δ, ppm:
spectrum, δ, ppm: 182.1 (C ), 137.0 (C ), 135.6 (C ),
47.3 (C ), 46.1 (C ), 134.2 (C ), 131.0 (C ), 41.8 (C ),
44.0 (C ), 47.0 (C ), 59.7 (C ), 49.5 (C ), 32.0 (C ).
Found, %: C 76.42; H 7.83. C H O . Calculated, %: C
2
5
11
7
6
4
1
2
3
4
5
2
8.08 (C ), 28.4 (C ), 29.6 (C ), 35.45 (C ), 35.92 (C ),
0.00 (C ), 42.12 (C ), 77.31 (C ), 135.4 (C ), 137.0 (C ),
3
1
2
10
9
6
7
8
9
10
4
8
1
68.3 (C ). Found, %: C 73.26; H 8.89. C H O .
1
1
16
2
13 16
2
Calculated, %: C 73.30; H 8.94.
76.44; H 7.89.
exo-5-Ethylbicyclo[2.2.1]hept-2-exo-yl acrylate
X). From 61 g of compound III, 43.2 g of acrylic acid,
REFERENCES
(
and 0.22 g of the catalyst at 80°C we obtained 71.0 g
20
1. Kobayashi, Kenichi and Kumagai, Tomohiro, US Patent
(
0
73%) of compound X, bp 136–137°C (30 mm Hg), d
4
.9866, n D2 0 1.4783. Found, %: C 74.15; H 9.29.
6576711, 2003; Ref. Zh. Khim., 2003, 24T254P.
2
. German Patent 10203122, 2003; Ref. Zh. Khim., 2005,
0O70P.
. French Patent 2898050, 2007; Ref. Zh. Khim., 2008, 7R2.44P.
. Japan Patent 61-53242, 1986; Ref. Zh. Khim., 1987, 9N66P.
. Neumann, C., Welt Farben., 2005, nos., 7, 8, p. 8.
. Mamedov, M.K., Dzhafarova, E.N., and Rasulova, R.A.,
C H O . Calculated, %: C 74.19; H 9.33.
12
18
2
2
exo-5-Isopropylbicyclo[2.2.1]hept-2-exo-yl
acrylate (XI).Amixture of 68 g of compound IV, 43.2 g
of acrylic acid, and 0.22 of the catalyst was heated at
3
4
5
6
8
1
0°C. We isolated 73.9 g (71%) of compound XI, bp:
20
20
42–143°C (30 mm Hg), d 0.9700, n 1.4790. Found,
4 D
Azerb. Khim. Zh., 2005, vol. 2, p. 116.
7. Mamedov, M.K., Rasulova, R.A., and Makhmudova, E.K.,
Azerb. Khim. Zh., 2007, vol. 4, p. 138.
%
: C 74.91; H 9.57. C H O . Calculated, %: C 74.96;
13 20 2
H 9.67.
exo-5-Propylbicyclo[2.2.1]hept-2-exo-yl acrylate
XII). From 68 g of compound V, 43.2 g of acrylic acid,
and 0.22 g of the catalyst at 80°C we obtained 75.8 g
8. Rasulova, R.A., Mamedov, M.K., andAzizov,A.G., Azerb.
Neft. Khoz., 2008, vol. 5, p. 53.
(
9. Mamedov, M.K., and Rasulova, R.A., Protsessy Neftekhim.
Neftepererab., 2008, nos. 3, 4, p. 185.
10. Mamedov, M.K., Gadzhieva, I.N., andAlimardanov, Kh.M.,
Zh. Org. Khim., 2003, vol. 39, p. 203.
1. Mamedov, M.K. and Rasulova, R.A., Zh. Org. Khim., 2006,
vol. 42, p. 1159.
2. Mamedov, M.K., Suleimanova, E.T. Neftekhimiya., 1991,
(
68%) of compound XII, bp 159–160°C (30 mm Hg),
2
0
20
d
0.9712, nD 1.4815. Found, %: C 74.92; H 9.61.
4
C H O . Calculated, %: C 74.96; H 9.67.
13
20
2
1
exo-5-Butylbicyclo[2.2.1]hept-2-exo-yl acrylate
XIII). A mixture of 75 g of compound VI, 43.2 g of
acrylic acid, and 0.22 g of the catalyst was heated at
(
1
vol. 31, p. 350.
8
1
0°C. We isolated 74.3 g (67%) of compound XIII, bp
1
3. Onishchenko, A.S., Dienovyi sintez (Dienic Synthsis),
20
20
79–180°C (30 mm Hg), d 0.9699, n 1.4833. Found,
4 D
Moscow: Izd.Akad. Nauk SSSR, 1963, p. 595.
%
: C 75.60; H 9.95. C H O . Calculated, %: C 75.63;
14 22 2
14. Goronovskii, I.T., Nazarenko, Yu.P., and Nekryach, E.F.,
Kratkii spravochnik po khimii (Concise Handbook on
Chemistry), Kiev: Naukova, dumka, 1974, p. 992.
15. Fieser, L. F. and Fieser, M., Reagents for Organic Synthesis,
NewYork: Wiley-Intersci., 1972.
H 9.70.
exo-5-Amylbicyclo[2.2.1]hept-2-exo-yl acrylate
XIV). A mixture of 82 g of compound VII, 43.2 g of
acrylic acid and 0.22 g of the catalyst was heated at
(
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 5 2010