ARTEM’EV et al.
1840
The aqueous phase was acidified with 35% aqueous
The IR spectra were recorded on a Bruker IFS-25
1
spectrometer from thin films. The H, 13C, and 31P
HCl to pH 1 and extracted with chloroform (3×
20 mL). The combined extracts were washed with
water (3×15 mL) and dried over Na2SO4, the solvent
was distilled off, and the residue was dried under
reduced pressure (35–40°C, 1 mm). Yield 3.38 g
(40%), yellowish oily substance. IR spectrum, ν, cm–1:
NMR spectra were measured on a Bruker DPX-400
instrument at 400.13, 101.61, and 161.98 MHz, respec-
tively, using CDCl3 as solvent and 85% H3PO4 as
external reference for 31P. Alkenes Ia–Ic were synthe-
sized by dehydration of the corresponding 1-phenyl-
alkan-1-ols in the presence of p-toluenesulfonic acid.
Red phosphorus was commercial product (KSAN SIA,
China).
1
2366 s (P–H), 1172 s (P=O). H NMR spectrum, δ,
3
ppm: 0.91 t (3H, Me, J = 6.7 Hz), 1.41–1.59 m and
1.66–1.80 m [4H, (CH2)2Me], 2.01–2.11 m (1H, CHP),
2.72–2.82 m and 3.08–3.16 m (1H each, CH2Ph),
7.04 d (1H, PH, 1J = 542 Hz), 7.26–7.37 m (5H, Ph),
12.08 br.s (1H, OH). 13C NMR spectrum, δC, ppm:
This study was performed under financial support
by the Russian Foundation for Basic Research (project
no. 12-03-31097-mol_a) and by the President of the
Russian Federation (Program for Support of Leading
Scientific Schools, project no. NSh-1550.2012.3).
3
13.9 (Me), 20.5 d (CH2Me, J = 8.6 Hz), 28.3 d
(CH2Et, 2J = 1.7 Hz), 33.0 (CH2Ph), 39.5 d (CHP, 1J =
95.7 Hz), 126.4 (Cp), 128.4 and 129.0 (Co, Cm), 138.6 d
3
(Ci, J = 12.4 Hz). 31P NMR spectrum: δP 41.86 ppm
REFERENCES
(1J = 542 Hz). Found, %: C 62.25; H 8.07; P 14.59.
C11H17O2P. Calculated, %: C 62.11; H 8.17; P 14.44.
1. Trofimov, B.A., Rakhmatullina, T.N., Gusarova, N.K.,
and Malysheva, S.F., Usp. Khim., 1991, vol. 60, p. 2619.
2. Gusarova, N.K., Arbuzova, S.N., and Trofimov, B.A.,
Pure Appl. Chem., 2012, vol. 84, p. 439.
3. Trofimov, B.A. and Gusarova, N.K., Mendeleev Com-
mun., 2009, vol. 19, p. 295.
Phosphinic acids IIb and IIc were synthesized in
a similar way from alkenes Ib and Ic.
1-Phenylhexan-2-ylphosphinic acid (IIb). Yield
38%, yellowish oily substance. IR spectrum, ν, cm–1:
1
2384 s (P–H), 1174 s (P=O). H NMR spectrum, δ,
ppm: 0.82 t (3H, Me, 3J = 7.1 Hz); 1.19–1.28 m, 1.30–
1.53 m, 1.60–1.75 m [6H, (CH2)3Me]; 1.92–2.02 m
(1H, CHP), 2.65–2.75 m and 3.00–3.09 m (1H each,
4. Trofimov, B.A., Malysheva, S.F., Rakhmatulina, T.N.,
Gusarov, A.V., and Gusarova, N.K., Zh. Obshch. Khim.,
1991, vol. 61, p. 1955.
5. Artem’ev, A.V., Malysheva, S.F., Korocheva, A.O., and
Bagryanskaya, I.Yu., Heteroatom Chem., 2012, vol. 23,
p. 568.
6. Malysheva, S.F., Belogorlova, N.A., Gusarova, N.K.,
Artem’ev, A.V., Albanov, A.I., and Trofimov, B.A.,
Phosphorus, Sulfur Silicon Relat. Elem., 2011, vol. 186,
p. 1688.
7. Trofimov, B.A., Dmitriev, V.I., Kazantseva, T.I., Shai-
khudinova, S.I., Malysheva, S.F., Sigalov, M.V., and
Gusarova, N.K., Zh. Obshch. Khim., 1990, vol. 60,
p. 2174.
8. Trofimov, B.A., Gusarova, N.K., Rakhmatulina, T.N.,
Malysheva, S.F., Lyavinets, A.S., and Voronkov, M.G.,
Zh. Obshch. Khim., 1991, vol. 61, p. 1310.
9. Trofimov, B.A., Gusarova, N.K., Malysheva, S.F.,
Rakhmatulina, T.N., Voronkov, M.G., Dmitriev, V.I., and
Shaikhudinova, S.I., Phosphorus, Sulfur Silicon Relat.
Elem., 1991, vol. 55, p. 271.
10. Gusarova, N.K., Malysheva, S.F., Rakhmatulina, T.N.,
Dmitriev, V.I., Shaikhudinova, S.I., Sinegovskaya, L.M.,
and Trofimov, B.A., Zh. Obshch. Khim., 1990, vol. 60,
p. 828.
11. Trofimov, B.A., Malysheva, S.F., Gusarova, N.K.,
Dmitriev, V.I., Shaikhudinova, S.I., Rakhmatulina, T.N.,
Donskikh, V.I., and Voronkov, M.G., Zh. Obshch. Khim.,
1989, vol. 59, p. 1894.
1
CH2Ph), 6.97 d (1H, PH, J = 539 Hz), 7.19–7.64 m
(5H, Ph), 11.60 br.s (1H, OH). 13C NMR spectrum, δC,
2
ppm: 13.7 (Me), 22.6 (CH2Me), 25.9 d (CH2Pr, J =
3
1.7 Hz), 29.4 d (CH2Et, J = 7.8 Hz), 33.0 (CH2Ph),
1
39.7 d (CHP, J = 94.8 Hz), 126.4 (Cp), 128.5 and
3
129.0 (Co, Cm), 138.6 d (Ci, J = 12.4 Hz). 31P NMR
spectrum: δP 41.11 ppm (1J = 539 Hz). Found, %:
C 63.70; H 8.46; P 13.69. C12H19O2P. Calculated, %:
C 63.64; H 8.61; P 13.49.
1-Phenylheptan-2-ylphosphinic acid (IIc). Yield
34%, yellowish oily substance. IR spectrum, ν, cm–1:
1
2383 s (P–H), 1155 s (P=O). H NMR spectrum, δ,
ppm: 0.81 t (3H, Me, 3J = 7.0 Hz); 1.14–1.25 m, 1.29–
1.51 m, 1.59–1.74 m [8H, (CH2)4Me]; 1.91–2.01 m
(1H, CHP), 2.65–2.74 m and 3.00–3.08 m (1H each,
1
CH2Ph), 6.96 d (1H, PH, J = 541 Hz), 7.18–7.29 m
(5H, Ph), 12.71 br.s (1H, OH). 13C NMR spectrum, δC,
ppm: 14.0 (Me), 22.4 (CH2Me), 26.3 (CH2Bu), 27.1 d
3
(CH2Pr, J = 7.8 Hz), 31.8 (CH2Et), 33.1 (CH2Ph),
1
39.9 d (CHP, J = 94.8 Hz), 126.5 (Cp), 128.6 and
3
129.2 (Co, Cm), 138.9 d (Ci, J = 12.5 Hz). 31P NMR
spectrum: δP 41.15 ppm (1J = 541 Hz). Found, %:
C 64.98; H 8.81; P 12.89. C13H21O2P. Calculated, %:
C 64.84; H 8.77; P 12.61.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 12 2013