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614
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spectrum, δ, ppm: 1.22 d [6Н, СН(СН3)2, J 6.2 Hz],
1.26–1.66 m (10Н, С3–7Н2), 2.24 t (2Н, С2Н2, J 7.3 Hz),
2.32 t (2Н, С8Н2, J 6.6 Hz), 4.99 septet [1Н, СН(СН3)2,
J 6.4 Hz], 9.80 s (1Н, ОН). 13С NMR spectrum, δ,
ppm: 21.78 q [CH(CH3)2], 24.67 t, 24.88 t, 28.85 t,
29.06 t, 29.63 t (С3–7Н2), 34.07 t, 34.58 t (С2Н2, С8Н2),
67.33 d [CH(CH3)2], 173.38 s (С1), 178.60 s (С9).
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8-Cyanooctanoic acid (14). Rf 0.19 (petroleum ether–
tert-butyl methyl ether, 2 : 1). IR and Н NMR spec-
trum are identic to those previously described [22].
1
Ozonolysis in a mixture of acetic acid and
dichloromethane. By method а after chromatogra-
phing 1.62 g of residue (petroleum ether–tert-butyl
methyl ether, 2 : 1) we obtained 0.36 g (46%) of
nonanoic acid 3, 0.36 g (45%) of nonanal oxime 6,
0.61 g (65%) of nonanedioic acid 2, and 0.25 g (26%)
of 9-(hydroxyimino)nonanoic acid 4.
9. Otsuki, H. and Funahashi, H., US Patent no. 2862940,
1958.
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By method b after chromatographing 1.86 g of
residue (SiO2, petroleum ether–tert-butyl methyl ether,
2 : 1) we obtained 0.60 g (75%) of nonanoic acid 3 and
1
0.64 g (74%) of nonanedioic acid 2, whose IR, Н and
13С NMR spectra were identic to those previously
described [17].
Ozonolysis in THF. By method a after chromato-
graphing 1.48 g of residue (SiO2, petroleum ether–tert-
butyl methyl ether, 2 : 1) we obtained 0.26 g (33%) of
nonanoic acid 3, 0.26 g (33%) of nonanal oxime 6,
0.32 g (34%) of nonandioic acid 2, and 0.31 g (33%)
of 9-(hydroxyimino)nonanoic acid 4.
15. Brinen, J.B. and Singh, B., J. Am. Chem. Soc., 1971,
vol. 93, p. 6623.
16. Ishmuratov, G.Yu., Shayakhmetova, A.Kh., Yakovle-
va, M.P., Legostaeva, Yu.V., Shitikova, O.V., Galkin, E.G.,
and Tolstikov, G.A., Russ. J. Org. Chem., 2007, vol. 43,
p. 1114.
17. Zimmermann, F., Meux, E., Mieloszynski, J.-L.,
Lecuire, J.-M., and Oget, N., Tetrahedron Lett., 2005,
vol. 46, p. 3201.
18. Yukawa, M., Sakai, Y., and Suzukr S., Bull. Chem. Soc.
Jpn., 1966, vol. 39, p. 2266.
19. Terent’ev, A.O., Kutkin, A.V., Starikova, Z.A., Anti-
pin, M.Yu., Ogibin, Yu.N., and Nikishina, G.I.,
Synthesis, 2004, p. 2356.
By method b after chromatographing 1.92 g of
residue (SiO2, petroleum ether–tert-butyl methyl ether,
2 : 1) we obtained 0.57 g (73%) of nonanoic acid 3 and
0.66 g (70%) of nonanedioic acid 2.
The study was carried out under the partial
financial support of the Program of the President of the
Russian Federation for supporting the leading
scientific schools (grant NSh-2625.2014.3 “Synthetic
transformations of substances obtained from domestic
raw material as the basic principle of developing
pharmaceuticals of high social importance”).
20. Adlof, R.O., Neff, W.E., Emken, E.A., and Pryde, E.H.,
J. Am. Oil Chem. Soc., 1977, vol. 54, p. 414.
21. Thomas, J.F. and Patrick, H., Tetrahedron Lett., 2010,
vol. 51, p. 5615.
22. Burns, T.P. and Rieke, R.D., J. Org. Chem., 1987, vol. 52,
p. 3674.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 5 2015