144
MALYSHEVA et al.
3
(CHPh, 1H, JHH 15.4), 7.28–7.43 m (5H, Ph). Found,
%: С 91.40; Н 8.41. C9H13О2P. Calculated, %: С
91.47; Н 8.53.
ACKNOWLEDGMENTS
This work was supported by the Russian Foundation
for Basic Research (grant no. 08-03-00251) and the
President of Russian Federation (the Program of
support of the leading scientific schools, grant no. NSh
3230-2010.3).
Bis(1-methyl-2-phenylethyl)phosphinic acid (II).
A mixture of red phosphorus (0.34 g, 11 mmol), ground
KOH·0.5H2O (0.84 g, 13 mmol), allylbenzene (1.56 g,
13 mmol), 15 ml of DMSO, 0.07 ml of Н2О, and
hydroquinone (0.03 g) was irradiated in a microwave
oven at 600 W for 6 min. The reaction mixture was
cooled, diluted with water (20 ml), and extracted with
chloroform. The aqueous layer was acidified with
concentrated aqueous НСl and extracted with chloro-
form (2×20 ml). The chloroform extracts were washed
with water (2×20 ml), dried over calcium chloride,
chloroform was removed, the residue was evacuated to
obtain 0.18 g (9%) of acid II, colorless oil. IR spec-
trum (film), ν, cm–1: 3441, 3083, 3060, 3024, 2955,
3000, 2850, 1603, 1495, 1453, 1387, 1377, 1253,
1144, 766, 756, 734, 707, 599, 483. 1Н NMR
spectrum, δ, ppm (J, Hz): 1.13-1.24 m (6H, Me), 2.40–
2.42 m (2H, CHP), 2.57–2.65 m (2H, CH2Ph), 3.43–
3.48 m (2H, CH2Ph), 7.11–7.34 m (10H, Ph). 13С
NMR spectrum, δС, ppm (J, Hz): 12.96, 13.01 and
REFERENCES
1. The Chemistry of Organophosphorus Compounds, Vol. 4:
Ter- and Quinque-Valent Phosphorus Acids and Their
Derivatives, Hartley, F.R., Ed., New York: Wiley, 1996,
p. 945.
2. Nifant’ev, E.E., Khimiya gidrofosforil’nykh soedinenii
(Chemistry of Hydrophosphoryl Compounds), Moscow:
Nauka, 1983.
3. Trofimov, B.A., Gusarova, N.K., and Brandsma, L.,
Main Group Chem. News, 1996, vol. 4, no. 1, p. 18.
4. Trofimov, B.A. and Gusarova, N.K., Mendeleev
Communn., 2009, vol. 19, p. 295.
5. 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.
2
13.07 d (Me, JPC 2.2), 32.64, 32.68, 32.73, 321.82 d
(PСН, JPC 57.5, 58.1, 57.6, 57.4), 36.25, 36.22 d
1
6. Trofimov, B.A., Malysheva, S.F., Gusarova, N.K.,
Kuimov, V.A., Belogorlova, N.A., and Sukhov, B.G.,
Tetrahedron Lett., 2008, vol. 49, p. 3480.
2
(СН2Ph, JPC 1.5), 126.70 (C-p), 128.88 (C-o), 129.19
(C-m), 139.66 d and 139.70 d (C-i, 3JPC 11.8 and 12.6).
31Р NMR spectrum, δР, ppm: 56.43. Found, %: С
71.65; Н 7.44; Р 10.05. C18H23О2P. Calculated, %: С
71.50; Н 7.67; Р 10.24.
7. Gusarova, N.K., Shaikhudinova, S.I., Kazantseva, T.I.,
Malysheva S.F., Sukhov, B.G., Belogorlova, N.A.,
Dmitriev, V.I., and Trofimov, B.A., Russ. J. Gen.
Chem., 2002, vol. 72, no. 3, p. 371.
IR spectra were recorded on a Bruker IFS-25
spectrometer. 1Н, 13С, 31Р NMR spectra were registered
on a Bruker DPX-400 spectrometer (400.13, 101.61,
161.98 MHz, respectively) in C6D6, external standard
85% Н3РО4 (31Р NMR). Microwave radiation was
performed in a microwave oven Samsung 181 DNR.
Commercial red phosphorus (KSAN “SIA,” China)
was used.
8. Trofimov, B.A., Dmitriev, V.I., Kazantseva, T.I.,
Shaikhudinova, S.I., Malysheva, S.F., Sigalov, M.V.,
and Gusarova, N.K., Zh. Obshch. Khim., 1990, vol. 60,
no. 9, p. 2174.
9. Trofimov, B.A., Shaikhudinova, S.I., Dmitriev, V.I.,
Nepomnyashchikh, K.V., Kazantseva, T.I., and Gusa-
rova, N.K., Russ. J. Gen. Chem., 2000, vol. 70, no. 1,
p. 40.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 81 No. 1 2011