TALYBOV
124
3. Kloetzing, R.J., Thaler, T., and Knochel, P., Org. Lett.,
2006, vol. 8, p. 1125.
4. Poisson, T., Belhomme, M.-C., and Pannecoucke, X.,
J. Org. Chem., 2012, vol. 77, p. 9277.
5. Masahiro, M., Yasuhiro, S., Kazuaki, K., Naotaka, S.,
131.9 (Carom). Found, %: C 75.94; H 5.39. C11H12O2.
Calculated, %: C 74.98; H 6.86.
Compounds 2 and 3 were synthesized in a similar
way.
1-[(Prop-2-yn-1-yl)oxy]-2-phenylpropan-2-ol (2).
Yield 62%, bp 101–102°C (2 mm), d420 = 1.0251, nD20 =
1.5384, MRD = 58.04, calcd. 53.31. IR spectrum, ν,
cm–1: 3598 (O–H), 3287, 2110 (C≡C), 3085, 3065,
3030, 1600, 1490, 1100 (C–O–C), 985, 700, 770 (Ph).
1H NMR spectrum, δ, ppm: 1.02 s (3H, CH3), 2.65 t
and Hideya, M., J. Org. Chem., 2013, vol. 78, p. 5843.
6. Jiang, B., Chen, Z., and Tang, X., Org. Lett., 2002,
vol. 4, p. 3451.
7. Trost, B.M. and Üeiss, A.H., Adv. Synth. Catal., 2009,
vol. 351, p. 963.
8. Anand, N.K. and Carriera, E.M., J. Am. Chem. Soc.,
2001, vol. 123, p. 9687.
9. Takita, R., Fukuta, Y., Tsuiji, R., Ohshima, T., and
Shibasaki, M., Org. Lett., 2005, vol. 7, p. 1363.
10. Lee, S.I., Kim, S.M., Kim, S.Y., and Chung, Y.K.,
Synlett, 2006, no. 14, p. 2256.
11. Schuler, M., Silva, F., Bobbio, C., and Tessier, A.,
4
(1H, ≡CH, J = 2 Hz), 3.46 br.s (1H, OH), 3.65 s (2H,
CH2O), 4.25 d (2H, OCH2C≡, 4J = 2 Hz), 7.25–7.75 m
(5H, Ph). 13C NMR spectrum, δC, ppm: 23.1 (CH3), 56
(≡CCH2O), 69 (≡CH), 75 (≡CCH2O), 80 (OCH2), 93.2
(COH), 126.0 (Carom), 126.8 (2C, Carom), 126.9 (2C,
Carom), 129.9 (Carom). Found, %: C 75.94; H 7.39.
C12H14O2. Calculated, %: C 75.76; H 7.42.
Angew. Chem., Int. Ed., 2008, vol. 47, p. 7927.
12. Akperova, M.A., Talybov, G.M., and Karaev, S.F., Izv.
Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol.,
2011, vol. 54, no. 8, p. 35.
13. Garayev, S.F. and Talybov, G.M., Science Without
Borders. Trans. Int. Acad. Sci., Baku–Insbruck,
2007/2008, vol. 3, p. 492.
14. Aliev, S.M., Sadykhov, K.I., Karaev, S.F., Taly-
bov, G.M., Gadzhieva, M.A., and Askerova, S.A., RU
Patent no. 2 015 136, 1994; Byull. Izobret., 1994, no. 12.
15. Karaev, S.F., Talybov, G.M., Egorov, V.V., and Tsali-
kova, Z.M., USSR Inventor’s Certificate no. 1 704 399,
1991; Byull. Izobret., 1992, no. 6.
1-{[(Prop-2-yn-1-yl)oxy]methyl}cyclopentan-1-ol
(3). Yield 67%, bp 101–102°C (2 mm), d420 = 1.0621,
nD20 = 1.4965, MRD = 42.42, calcd. 42.96. IR spectrum,
ν, cm–1: 3605 (O–H), 3289, 3082, 3065, 3031, 2100
(C≡C), 1604, 1490, 1100 (C–O–C), 985, 700, 770
1
(Ph). H NMR spectrum, δ, ppm: 1.15–1.23 m [8H,
4
(CH2)4], 2.65 t (1H, ≡CH, J = 2 Hz), 3.44 s (2H,
CH2O), 3.47 br.s (1H, OH), 4.15 d (2H, OCH2C≡, 4J =
13
2 Hz). C NMR spectrum, δC, ppm: 24 (2C, CH2), 32
(2C, CH2), 56 (≡CCH2O), 69 (≡CH), 75 (≡CCH2O),
80 (OCH2), 96.2 (COH). Found, %: C 70.24; H 9.49.
C9H14O2. Calculated, %: C 70.1; H 9.15.
16. Naibova, T.M., Bilalov, Ya.M., Talybov, G.M., and
Karaev, S.F., Plast. Massy, 2004, no. 11, p. 34.
The IR spectra of 1–3 were recorded on a Specord
17. Karaev, S.F., Bilalov, Ya.M., Naibova, T.M., Taly-
bov, G.M., and Nurieva, U.G., Fizikokhim. Poverkh.
Zashch. Mater., 2010, vol. 46, p. 393.
18. Silverstein, R.M., Bassler, G.C., and Morrill, T.C.,
Spectrometric Identification of Organic Compounds,
New York: Wiley, 1974, 3rd ed.
75 IR spectrometer from solutions in carbon tetra-
13
chloride. The 1H and C NMR spectra were measured
on a Bruker SF-300 instrument at 300.13 and 75 MHz,
respectively, using CDCl3 as solvent and hexamethyl-
disiloxane as internal standard.
19. Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR-
spektroskopiya v organicheskoi khimii (NMR Spectros-
copy in Organic Chemistry), Leningrad: Khimiya, 1983.
20. Structure Determination of Organic Compounds: Tables
of Spectral Data, Pretsch, E., Bühlmann, P., and
Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed.
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 1 2017