4
48
POPOV et al.
hydride in 40 mL of THF, 14 g (0.1 mol) of compound
cheskoi khimii (Experimental Methods in Organic
Chemistry), Moscow: Khimiya, 1968, p. 28.
4. Franzus, B. and Snyder, E.I., J. Am. Chem. Soc., 1965,
XII, and 8 g (0.063 mol) of anhydrous NiCl 7 g
2
(
58%) of the product XIII was obtained, colorless
vol. 87, p. 3423.
liquid, bp 174–175°C (reported data 174°C [22]).
5
6
7
8
. Alonso, F., Osantey, I., and Yus, M., Tetraherdon,
007, vol. 63, p. 93.
. Boudjahem, A.G., Monteverdi, S., Mercy, M., and
Bettahar, M.M., Langmuir, 2004, vol. 20, no. 1, p. 208.
. Dong-Hwang, Chen and Szu-Han, Wu, Chem. Mater.,
2
-Carboxynorbornane XVa. The unsaturated acid
XIVa, 20 g, was dissolved in a solution of 8 g
0.2 mol) of sodium hydroxide in 50 mL of water.
2
(
After that 25 g (0.5 mol) of hydrazine hydrate was
added, the obtained mixture was heated to 60°C, and a
solution of 4 g (0.017 mol) of NiCl ·6H O in 15 mL of
water was added in portions. The obtained black
solution was stirred for 4 h at 60°C. Then the reaction
mixture was cooled, and a solution of 24.5 g
2
000, vol. 12, no. 5, p. 1354.
2
2
. Groschel, L., Haidar, R., Beyer, A., Reichert, K.H., and
Schomacker, R., Catal. Lett., 2004, vol. 95, nos. 1–2,
p. 67.
. Belykh, L.B., Titova, Yu.Yu., Rokhin, A.V., and
Schmidt, F.K., Russ. J. Appl. Chem., 2010, vol. 83,
no. 11, p. 1911.
9
(
0.25 mol) of sulfuric acid in 20 mL of water was
added. The product was extracted with diethyl ether,
the solvent was distilled off, and the residue was
distilled in a vacuum to give 15.2 g (75%) of acid
XVa, colorless crystals, mp 60–61°C, bp 147–149°C
10. Schmidt, F.K., Titova, Yu.Yu., Belykh, L.B., Uma-
nets, V.A., Buyanov, R.A., and Khutsishvili, S.S., Russ.
J. Gen. Chem., 2012, vol. 82, no. 8, p. 1334.
(
20 mm Hg) (reported data: endo-isomer mp 63–65°C,
11. Lukashevich, A.I., Molchanov, V.V., Godin, V.V.,
Tolstikov, G.A., and Buyanov, R.A., Chem. Sustainable
Development, 2002, vol. 10, p. 109.
1
exo-isomer mp 54–56°C [23]). H NMR spectrum, δ,
ppm: 1.09–1.80 m (8H, 4CH ); 2.21–2.29 m (1H, CH),
2
(
2
1
1
1
1
1
1
2. Dzhemilev, U.M., Vostrikova, O.S., and Tolstikova, G.A.,
Russ. Chem. Rev., 1990, vol. 59, no. 12, p. 1157.
3. Gao, F. and Hoveyda, A., J. Am. Chem. Soc., 2010,
vol. 132, no. 32, p. 10961.
4. Eiseh, J.J., Ma, X., Singh, M., and Wilke, G., J. Organomet.
Chem., 1997, vol. 527, p. 301.
5. Balcom, D. and Furst, A., J. Am. Chem. Soc., 1953,
vol. 75, no. 17, p. 4334.
6. Furst, A., Berlo R.C., and Hooton S., Chem. Rev., 1965,
.53 s (1H, CH); 2.68–2.75 m (1H, CHCO), 12.2 s
1H, COOH).
Isobutyric acid XVb. Analogously to the synthesis
of compound XVa from 20 g (0.233 mol) of acid
XIVb, 12 g (0.3 mol) of sodium hydroxide, 25 g
(
NiCl · 6H O in 60 ml of water 14.2 g (70%) of acid
XVb was obtained as a colorless liquid, bp 152–155°C,
0.5 mol) of hydrazine hydrate, and 3 g (0.013 mol) of
2
2
2
0
20
nD 1.3933 (reported data bp 154.4°C, nD 1.3930
22]).
vol. 65, p. 51.
[
7. Brown H.C. and Yoon, N.M., J. Am. Chem. Soc., 1966,
vol. 88, p. 1464.
3
-Phenylpropionic acid XVc. Analogously to the
synthesis of compound XVa from 15 g (0.1 mol) of
unsaturated acid XIVc, 6 g (0.15 mol) of sodium
hydroxide, 18 g (0.36 mol) of hydrazine hydrate, and
18. Schleyer, P.R., Donaldson, M.M., Nicholas, R.D., and
Cupas, C., Org. Synth., 1962, vol. 42, p. 9.
19. Bruson, H.A. and Riener, T.W., J. Am. Chem. Soc.,
3
g (0.013 mol) of NiCl ·6H O in 60 mL of water 10 g
1948, vol. 70, no. 8, p. 2809.
2
2
(
67%) of hydrogenation product XVc was obtained as
20. Oldenziel, O.H., van Leusen, D., and van Leusen, A.M.,
colorless crystals, mp 49°C, bp 279–281°C (reported
data mp 48.6°C, bp 279.6°C [24]).
J. Org. Chem., 1977, vol. 42, no. 19, p. 3114.
21. Berson, J.A., Remanick, A., Suzuki, S., Reynonds-
Warnhoff, P., and Willner, D., J. Am. Chem. Soc., 1961,
vol. 83, p. 3986.
REFERENCES
2
2. Khimicheskaya entsiklopediya (Chemical Encyclopedy),
Knunyants, I.L., Ed., Moscow: Sovetskaya Entsiklo-
pediya, 1988, vol. 2 p. 17.
1
2
3
. Augustine, R.L., Catalytic Hydrogenation, New York:
Marcel Dekker, 1965, ch. 4, p.1.
. Brown, H.C. and Murray, K.J., J. Am. Chem. Soc.,
23. Bartlett, P.D. and Pincock, R.E., J. Am. Chem. Soc.,
1962, vol. 84, no. 12, p. 2445.
24. Ingersoll, A.W., Org. Synth., 1929, vol. 9, p. 43.
1
959, vol. 81, no. 15, p. 4108.
. Weygand-Hilgetag, Metody eksperimenta v organi-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014