HYDROGENATION OF ALKENES OVER NICKEL NANOPARTICLES
323
Chroman-2-one (26) was obtained from 26.4 g
0.18 mol) of coumarin (25) using 1 g (28 mmol) of
2. Hudlicky, M., Reductions in Organic Chemistry,
Chichester: Ellis Horwood, 1984, p. 309.
(
NaBH , 20 mL of propan-2-ol, and 1.8 g (14 mmol) of
NiCl ; 6 h, 40°C. Yield 24.9 g (94%). Mass spectrum,
3. Hartley, F.R. and Jardine, F.H., The Metal–Carbon
Bond, New York: Wiley, 1987, vol. 4, p. 1349.
4
2
m/z (I , %): 148 (100), 120 (60), 91 (43), 79 (12).
4. Sergeev, G.B., Ross. Khim. Zh., 2002, vol. 46, no. 5,
rel
p. 22.
Cyclohexylacetonitrile (29) was obtained from
5. Polshettiwar, V. and Varma, R.S., Green Chem., 2010,
1
6
2.1 g (0.1 mol) of a mixture of nitriles 27 and 28; 7 h,
vol. 12, p. 743.
5°C. Yield 8.4 g (0.068 mol, 68%), bp 110–112°C
1
6
. Deghedi, L., Basset, J.-M., Candy, J.-P., Dalmon, J.-A.,
(
(
20 mm). H NMR spectrum, δ, ppm: 1.15–1.75 m
10H, CH ), 1.97 m (1H, CH), 2.38 d (2H, CH CN,
Dubreuil, A.-C., and Fischer, L., Chem. Eng. Trans.,
2
2
2
009, vol. 17, p. 31.
J = 8.6 Hz).
2
,6
7. Hemantha, H.P. and Sureshbabu, V.V., Org. Biomol.
Chem., 2011, vol. 9, p. 2597.
8. Alonso, F., Osantey, I., and Yus, M., Tetrahedron, 2007,
Tricyclo[5.2.1.0 ]decane (31) was obtained from
2
6.4 g (0.2 mol) of dicyclopentadiene (30); 6 h, 40°C.
1
Yield 24.9 g (95%), bp 192–193°C [19]. H NMR
vol. 63, p. 93.
spectrum, δ, ppm: 1.20 t (2H, CH , J = 8.4 Hz), 1.25–
2
9
. Alonso, F., Candela, P., Gomez, C., and Yus, M., Adv.
Synth. Catal., 2003, vol. 345, p. 275.
1
.58 m (10H, CH ), 2.02 s (2H, CH), 2.27 s (2H, CH).
2
Bicyclo[2.2.1]heptane-2-carbonitrile (33) was ob-
tained from 15.75 g (0.15 mol) of nitrile 32; 6 h, 50°C.
1
0. Rangheard, C., de Julián Fernández, C., Phua, P.-H.,
Hoorn, J., Lefort, L., and de Vries, J.G., Dalton Trans.,
Yield 11.2 g (70%), bp 191–193°C, mp 47–50°C [23].
2
010, vol. 39, p. 8464.
1
H NMR spectrum, δ, ppm: 0.93–1.04 m (2H, CH2),
1
1. Popov, Yu.V., Mokhov, V M., and Nebykov, D.N., Russ.
1
2
.17–1.53 m (6H, CH ), 2.24–2.37 m (2H, CH), 2.52–
.68 m (1H, CHCN).
2
J. Gen. Chem., 2014, vol. 84, p. 444.
2. Mokhov, V.M., Popov, Yu.V., and Nebykov, D.N., Russ.
J. Gen. Chem., 2014, vol. 84, p. 622.
1
Hydrogenation of α-pinene. The reaction mixture
obtained from 0.36 g (10 mmol) of NaBH , 20 mL of
4
13. Hou, Y., Kondoh, H., Ohta, T., and Gao, S., Appl. Surf.
Sci., 2005, vol. 241, p. 218.
propan-2-ol, 0.65 g (5 mmol) of NiCl , and 34.4 g
2
(
0.25 mol) of α-pinene (34) after bubbling hydrogen
for 5 h at 50°C contained 45% of 2,6,6-trimethylbi-
cyclo[3.1.1]heptane (36). Mass spectrum, m/z (I , %):
38 (3) [M] , 95 (91), 81 (93), 67 (100), 55 (58),
1 (34).
1
4. Tee, Y.-H., Bachas, L., and Bhattacharyya, D., J. Phys.
Chem. C, 2009, vol. 113. p. 9454.
rel
15. Borodzinski, J.J. and Lasia, A., J. Appl. Electrochem.,
994, vol. 24, p. 1267.
1
+
1
4
1
6. Glavee, G.N., Klabunde, K.J., Sorensen, C.M., and
Hydrogenation of β-pinene. The reaction mixture
Hadjipanayis, G.C., Langmuir, 1994, vol. 10, p. 4726.
obtained from 0.5 g (14 mmol) of NaBH , 20 mL of
17. Couto, G.G., Klein, J.J., Schreiner, W.H., Mosca, D.H.,
de Oliveira, A.J.A., and Zarbin, A.J.G., J. Colloid
Interface Sci., 2007, vol. 311, p. 461.
4
propan-2-ol, 1 g (8 mmol) of NiCl , and 27.2 g
2
(
0.2 mol) of β-pinene (35) after bubbling hydrogen
for 5 h at 50°C contained 47% of 36. Mass spectrum,
18. Polshettiwar, V., Baruwati, B., and Varma, R.S., Green
Chem., 2009, vol. 11, p. 127.
+
m/z (I , %): 138 (8) [M] , 95 (88), 81 (100), 67 (47),
rel
4
1 (34).
19. Schleyer, P., Donaldson, M.M., Nicholas, R.D., and
Cupas, C., Org. Synth., 1962, vol. 42, p. 8.
2
,2,3-Trimethylbicyclo[2.2.1]heptane (38). The
2
0. Mackay, D., Shiu, W.-Y., Ma, K.-Ch., and Lee, S.Ch.,
Handbook of Physical-Chemical Properties and En-
vironmental Fate for Organic Chemicals, Boca Raton,
FL: CRC/Taylor & Francis, 2006, 2nd ed., p. 258.
reaction mixture obtained from 0.5 g (14 mmol) of
NaBH , 20 mL of propan-2-ol, 0.9 g (7 mmol) of
NiCl , and 25 g (0.184 mol) of camphene (37) after
bubbling hydrogen for 6 h at 50°C contained 56%
4
2
+
21. Spravochnik khimika (Chemist’s Handbook), Nikol’-
of 38. Mass spectrum, m/z (I , %): 138 (18) [M] , 109
rel
skii, B.P., Ed., Leningrad: Khimiya, 1971, vol. 2.
(
67), 95 (100), 82 (30), 67 (47), 41 (53).
2
2. Gardner’s Commercially Important Chemicals: Syno-
nyms, Trade Names, and Properties, Milne, G.W.A.,
Ed., Hoboken, NJ: Wiley, 2005, p. 169.
REFERENCES
1
. Augustine, R.L., Catalytic Hydrogenation, New York:
23. Bruson, H.A. and Reiner, T.W., J. Am. Chem. Soc.,
Marcel Dekker, 1965, vol. 4, p. 11.
1948, vol. 70, p. 2809.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 52 No. 3 2016