EFFECT OF THE STRUCTURE OF FUNCTIONALIZED PHOSPHORYL CARRIERS
1543
the procedure described in [24]. mp 84 C, and the solvent was removed on a rotary evaporator.
P
0
5
8
9.9 ppm (chloroform). Published data [24]: mp 85
6 C, 59.4 ppm.
Yield 26.4 g (76%), n2 1.4511,
25.7 ppm.
P
D
P
ACKNOWLEDGMENTS
Didecyl hydrogen phosphate (VIII). Nitrogen
dioxide obtained by the action of concentrated nitric
acid on a saturated solution of sodium nitrite was
barboted through a solution of 15 g of didecyl hydro-
gen phosphite in 20 ml of benzene until an intense
yellow color appeared. Benzene was removed on a
rotary evaporator, and the solid precipitate was twice
recrystallized from hexane to obtain 10 g (60%) of
compound VIII as colorless crystals. mp 47 C {pub-
The work was financially supported by the Russian
Foundation for Basic Research (project no. 04-03-
3
2906), Universities of Russia Basic Research Prog-
ram of the Ministry of Education and Science of the
Russian Federation, and Basic Research & Higher
Education Bilateral Program of the Ministry of Educa-
tion and Science of the Russian Federation and CRDF
(project no. REC 007).
lished data [25]: mp 46 47 C),
form).
0.9 ppm (chloro-
P
REFERENCES
Bis(2-ethylhexyl) diethylphosphoramidate (X).
Carbon tetrachloride, 7.546 g, was added dropwise to
a mixture of 15 g of bis(2-ethylhexyl) hydrogen phos-
phite and 8.96 g of diethylamine at 0 5 C. The reac-
tion mixture was let to stand for 30 min at this tem-
perature and then for 1 h at room temperature, the
amine hydrochloride was filtered off on a glass frit
and washed with hexane, the filtrate was washed with
1
. Nikolotova, Z.I. and Kartasheva, N.A., Ekstraktsiya
neitral’nymi organicheskimi soedineniyami: Spra-
vochnik po ekstrak-tsii (Extraction with Neutral
Organic Compounds: Handbook on Extraction),
Rozen, A.M., Ed., Moscow: Atomizdat, 1976.
2. Kron, T.E. and Tsvetkov, E.N., Usp. Khim., 1990,
vol. 59, no. 3, p. 483.
5
% HCl and twice with water, and dried with Na SO .
2 4
3. Garifzyanov, A.R., Zakharov, S.V., Kryukov, S.V.,
The solvent was removed in a vacuum, and the re-
sidue was distilled in a vacuum, bp 132 C (0.15 mm
Hg), to obtain 16 g (87%) of amide X, n 1.4421,
Galkin, V.I., and Cherkasov, R.A., Zh. Obshch. Khim.,
2
005, vol. 75, no. 8, p. 1273.
2
0
D
4
. Garifzyanov, A.R., Zaharov, S.V., and Cherka-
sov, R.A., Zh. Obshch. Khim., 2005, vol. 75, no. 7,
p. 1118.
1
1 ppm.
P
Bis(2-ethylhexyl) dibutylphosphoramidate (IX)
was synthesized in a similar way from 25 g of bis(2-
ethylhexyl) hydrogen phosphite, 26.34 g of dibutyl-
5. Garifzyanov, A.R., Shirshova, N.V., and Cherka-
sov, R.A., Zh. Obshch. Khim., 2005, vol. 75, no. 4,
p. 575.
amine in 10 ml of hexane, and 8 ml of CCl in 20 ml
4
of hexane. Yield 30.5 g (88%), bp 159 C (0.3 mm
6. Chibizov, V.P., Sovremennye metody razdeleniya i
opredeleniya radioaktivnyh elementov: Sb. nauch.
trudov (Modern Methods of Separation and Determina-
tion of Radioactive Elements: Collection of Scientific
Works), Moscow: Nauka, 1989, p. 128.
Hg), n2 1.4461,
0
10.7 ppm.
D
P
Bis(2-ethylhexyl) butylphosphoramidate (XI)
was synthesized in a similar way from 25 g of bis(2-
ethylhexyl) hydrogen phosphite, 14.9 g of dibutyl-
7
. Kormachev, V.V. and Fedoseev, M.S., Preparativ-
naya khimiya fosfora (Preparative Chemistry of
Phosphorus), Perm: Ural Branch Russ. Akad. Sci.,
amine in 10 ml of hexane, and 8 ml of CCl in 20 ml
4
of hexane. Yield 26.5 g (86%), bp 157 C (0.2 mm
Hg), n2 1.4455,
0
11.3 ppm.
D
P
1
992.
Bis(2-ethylhexyl) (N-butyl-N-octylamino)me-
thylphosphonate (XII) was synthesized as described
in [3].
8. Zakharov, S.V., Nuriazdanova, G.H., Garifzya-
nov, A.R., Galkin, V.I., and Cherkasov, R.A., Zh.
Obshch. Khim., 2004, vol. 74, no. 6, p. 946.
9
. Atherton, F.R., Openshaw, H.T., and Todd, R.R.,
J. Chem. Soc., 1945, no. 2, p. 660.
Didecyl (N,N-dibutylamino)methylphosphonate
(
XIII). Paraform, 2.3 g, was gradually added to a
mixture of 25 g of didecyl hydrogen phosphite and
.9 g of dibutylamine, heated on a boiling water bath,
1
0. Whitney, D.C. and Diamond, R.M., J. Phys. Chem.,
963, vol. 67, no. 2, p. 209.
1
8
the mixture was heated at 80 C until Paraform had
dissolved completely and then heated on a boiling
water bath for 1 h. After cooling, the reaction mixture
was diluted with equal volume of benzene, the result-
ing solution was passed through a column of Al O ,
11. Corbridge, D.E., Phosphorus. An Outline of its
Chemistry, Biochemistry and Technology, Amsterdam:
Elsevier, 1980.
12. Bredikhin, A., Tsubrik, O., Sillard, R., and Maeorg, U.,
SYNLETT, 2005, no. 12, p. 1939.
2
3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 10 2006