Synthesis and acylation of O,O-Dihexyl(dioctyl)-[1-hydroxy-3-(ethyl, diethylamino)-2,2-dimethylpropyl]phosphonates

Article abstract of DOI:10.1134/S1070363213070062

Reaction of dialkyl phosphites with 3-ethylamino- or 3-diethylamino- substituted aldehydes results in the corresponding 3-amino-1- hydroxyalkylphosphonates. The composition and structure of the obtained compounds were confirmed by elemental analysis, NMR

Full text of DOI:10.1134/S1070363213070062

ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 7, pp. 1336–1340. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © M.B. Gazizov, R.N. Burangulova, R.I. Minnekhanov, R.A. Khairullin, N.G. Aksenov, 2013, published in Zhurnal Obshchei Khimii,
2013, Vol. 83, No. 7, pp. 1083–1087.
Synthesis and Acylation of O,O-Dihexyl(dioctyl)-[1-hydroxy-
3-(ethyl, diethylamino)-2,2-dimethylpropyl]phosphonates
M. B. Gazizov, R. N. Burangulova, R. I. Minnekhanov, R. A. Khairullin, and N. G. Aksenov
Kazan National Research Technological University, ul. K. Marksa 68, Kazan, Tatarstan, 420015 Russia
e-mail: mukattisg@mail.ru
Received July 2, 2012
Abstract—Reaction of dialkyl phosphites with 3-ethylamino- or 3-diethylamino-substituted aldehydes results
in the corresponding 3-amino-1-hydroxyalkylphosphonates. The composition and structure of the obtained
compounds were confirmed by elemental analysis, NMR spectroscopy and chemical transformations.
DOI: 10.1134/S1070363213070062
Previously we have synthesized 3-amino-1-hydroxy-
alkylphosphonates containing MeO and EtO sub-
stituents at the P(IV) atom, which showed weak
bactericidal activity [1]. It is known that the com-
plexing ability of organophosphorus compounds includ-
ing those containing amino group increases signi-
ficantly as the number of substituents at the atom
P(IV) increases [2].
carbon substituents with 3-ethylamino- or 3-diethyl-
aminoaldehydes I and the acylation of the reaction
products with different acylating agents.
Reactions of dialkylphosphorous acids IIa, IIb with
3-alkylamino-substituted aldehydes Ia, Ib occur in the
absence of a catalyst with a small exothermic effect. It
is known that the Abramov reaction [3] proceeds in the
presence of bases as a catalyst. The formation of
phosphonates III in the absence of a catalyst is caused
by the nucleophilic catalysis by the secondary or
tertiary amino group present in the starting aldehyde
I.
Aiming to synthesize polyfunctional aminophos-
phoryl organic compounds with more pronounced
applied properties, we have studied the interaction of
dialkyl phosphites II containing long-chain hydro-
EtR1NCH2CMe2CHO + (R2O)2PHO
EtR1NCH2CMe2CH(OH)P(O)(OR2)2
I
II
IIIа−IIIc
I, R1 = H (а), Et (b); II, R2 = Hex (а), Oct (b); III, R1 = Et, R2 = Hex (а), Oct (b); R1 = H, R2 = Hex (c).
The composition and structure of phosphonates
IIIa–IIIc were confirmed by elemental analysis and
1H, 31P NMR spectra. The 31P NMR spectra of
compounds IIIa–IIIc contain the only signal in the
range of 24.2–24.5 ppm.
acylating agents: dichloroacetic acid IV, carboxylic
acid chlorides VI, and acetic anhydride X.
The interaction of phosphonate III with dichloro-
acetic acid IV results in stable salts (3-hydroxy-3-O,O-
dialkylphosphoryl-2,2-dimethylpropyl)ethyl- and
diethylammonium dichloroacetates V as syrupy sub-
stances. The acylation on the N–H and O–H bonds
does not occur.
In order to prove the structure of compounds III by
chemical transformations and to synthesize new P- and
N-containing polyfunctional organic compounds we
studied different reactions of phosphonates with
EtR1NCH2CMe2CH(OH)P(O)(OR2)2 + CHCl2COOH
CHCl2COO−EtR1N+CH2CMe2CH(OH)P(O)(OR2)2
III
V
IV
H
V, R1 = Et, R2 = Hex (a), Oct (b); R1 = H, R2 = Hex (c).
1336

SYNTHESIS AND ACYLATION OF O,O-DIHEXYL(DIOCTYL)-[1-HYDROXY-3-….
1337
The reactions were carried out by mixing the
reactants in anhydrous diethyl ether while cooling and
maintaining the reaction mixture at room temperature
for 1 day. After removing the solvent and volatile
components in a high vacuum salts V were obtained as
syrupy substances whose composition and structure
3.15–3.40 ppm. The presence of the absorption bands
at 2500 and 2673 cm–1 in the IR spectra corresponding
to the vibrations of N+H fragment confirms the
proposed structure of salts V [4].
Studies of acylation of phosphonates III with
benzoyl chloride VIa and 4-(chloroformyl)azinium
chloride (isonicotinoyl chloride hydrochloride) VIb
showed that depending on the structure of amino-
phosphonate and the reagents ratio occurs O-, N- and
N,O-acylation.
1
were confirmed by elemental analysis, IR, H, and 31P
NMR spectra.
The 31P NMR spectra of the salts V contain a
singlet signals in the range of 20.5–25.4 ppm
corresponding to the nearest environment of the
1
phosphorus atom O2P(O)C. The H NMR spectra of
The interaction of О,О-dialkyl [1-hydroxy-3-
(diethylamino)-2,2-dimethylpropyl]phosphonates IIIa,
IIIb with acylating agents VI in a ratio of 1:1 gives
rise to the O-acylation product VII.
salts V are given in the experimental section. It should
be noted that the transformation N(III) → N+(IV)
causes a downfield shift of the resonance signals of the
hydrogen atoms of methylene groups 2.25–2.75 →
IIIа, IIIb + PhCOCl + Et3N
Et2NCH2CMe2CH(OCOPh)P(O)(OR)2
HCl
−Et3N
VIа
VIIа, VIIb
N+
VIb
COClCl−
Et2NCH2CMe2CH(OCO
VIIc, VIId
H
IIIа, IIIb +
+ 2Et3N
N)P(O)(OR)2
−2Et3N HCl
R = Hex (а, c), Oct (b, d).
1
The reaction was carried out in a solution of
anhydrous diethyl ether or THF at room temperature in
the presence of triethylamine. After the removal of
triethylamine hydrochloride, distilling off the solvent
and volatile components in a high vacuum, the
products VII were identified in a crude form because
of their thermal lability. The composition and structure
of compounds VII were confirmed by elemental
analysis, H and 31P NMR spectra. The 31P NMR
spectra are characterized by the presence of one singlet
signal at 19.58–24.58 ppm, corresponding to phos-
phonate structure of compounds VIIa–VIId.
The acylation of phosphonate IIIc with compounds
VI in a 1:1 ratio of the reactants in the presence of
triethylamine affords N-acylation product VIII.
IIIc + PhCOCl + Et3N
Et(PhCO)NCH2CMe2CH(OH)P(O)(OHex)2
HCl
−Et3N
VIа
VIIIа
N+
COClCl−
H
Et(N
IIIc +
+ 2Et3N
CO)NCH2CMe2CH(OH)P(O)(OHex)2
−2Et3N HCl
VIb
VIIIb
The 31P NMR spectra of compounds VIIIa, VIIIb
are characterized by the presence of a singlet signal at
23.3–24.7 ppm.
Reaction of compound IIIc with a double excess of
benzoyl chloride VIa in THF at reflux results in the
N,O-diacylation product.
Et(PhCO)NCH2CMe2CH(OCOPh)P(O)(OHex)2
IIIc + 2PhCOCl + 2Et3N
HCl
−2Et3N
VIа
IX
The N,O-diacylation product is also formed in the
reaction of phosphonate IIIc with two equivalents of
acetic anhydride X at 90°C.
The composition and structure of compounds IX,
1
XI were proved by elemental analysis, H and 31P
NMR spectra. The 31P NMR spectra are characterized
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 7 2013

1338
GAZIZOV et al.
IIIc + 2(MeCO)2O
Et(MeCO)NCH2CMe2CH(OCOMe)P(O)(OHex)2
X
XI
by the presence of only a singlet at 20.9–25.3 ppm,
corresponding to the structure of phosphonate.
br.s (2Н, ОН, NH). 31P NMR spectrum: δP 24.18 ppm.
Found, %: N 3.75; P 8.12. C19H42NO4P. Calculated, %:
N 3.69; P 8.16.
EXPERIMENTAL
(3-Hydroxy-3-O,O-dihexylphosphoryl-2,2-dimethyl-
propyl)diethylammonium dichloroethanoate (Va).
To a solution of 1.2 g (3 mmol) of О,О-dihexyl (1-
hydroxy-3-diethylamino-2,2-dimethylpropyl)phosphonate
IIIa in 10 ml of anhydrous ether while stirring and
cooling with cold water was added dropwise 0.387 g
(3 mmol) of dichloroacetic acid IV. The reaction
mixture gradually warmed to room temperature and
was left standing for 2 days. Then the solvent and
volatile components were removed in a high vacuum.
The 1H NMR spectra were recorded on a Tesla BS-
567A spectrometer operating at 100 MHz and on a
Bruker MSL-400 instrument operating at 400 MHz.
Chemical shifts were measured relative to the residual
proton signals of the deuterated solvents (CDCl3,
acetone-d6, and DMSO-d6). The 31P NMR spectra were
recorded on a Bruker MSL-400 (162 MHz) and Bruker
WN-250 (101 MHz) spectrometers, external reference
85% H3PO4. The IR spectra were registered on a
Perkin Elmer Spectrum 65 FT-IR spectrometer in the
range of 400–4000 cm–1 (NaCl prism, thin layer,
mineral oil).
1
Yield 1.51 g (95.2%). H NMR spectrum (CDCl3), δ,
ppm: 0.8–1.75 m (34H, 2C5H11, 2NCH2Ме, CMe2),
2.9–3.4 m (6H, NCH2, 2NCH2Ме), 4.0 m (5H, 2OCH2,
PCH), 5.8 s (1H, CHCl2), 9.05 br. s (2H, N+H, OH).
31P NMR spectrum: δP 25.4 ppm. Found, %: N 2.67; P
5.84; Cl 13.27. C23H48NO6Cl2P. Calculated, %: N 2.61;
P 5.77; Cl 13.22.
О,O-Dihexyl (1-hydroxy-3-diethylamino-2,2-di-
methylpropyl)phosphonate (IIIа). To 2.5 g (16 mmol)
of 3-diethylamino-2,2-dimethylpropanal Ia was added
dropwise 4 g (16 mmol) of dihexylphosphorous acid
IIa. There was a temperature rise to 45°C. The mixture
was kept at room temperature for 48 h. Then the
volatile components were removed in a high vacuum
(3-Hydroxy-3-O,O-dioctylphosphoryl-2,2-dimethyl-
propyl)diethylammonium dichloroethanoate (Vb)
was prepared similarly from 1.8 g (4 mmol) О,О-di-
octyl (1-hydroxy-3-diethylamino-2,2-dimethylpropyl)-
phosphonate IIIb and 0.5 g (4 mmol) of dichloroacetic
1
to give 6.2 g (95.4%) of phosphonate IIIa. H NMR
spectrum (CDCl3), δ, ppm: 0.25–1.25 m (34H, 2C5H11,
2NCH2Me, CМe2), 2.25 m (6H, NCH2, 2NCH2Me),
3.7 m (6H, 2OCH2, PCH, ОН). 31P NMR spectrum: δP
24.3 ppm. Found, %: N 3.43; P 7.59. C21H46NO4P.
Calculated, %: N 3.36; P 7.51.
1
acid IV. Yield 2.1 g (91.3%). H NMR spectrum
(CDCl3), δ, ppm: 0.8–1.75
m
(42H, 2C7H15,
2NCH2Ме, CMе2), 3.1–3.6 m (6H, NCH2, 2NCH2Ме),
4.0 m (5H, 2OCH2, PCH), 5.8 s (1H, CHCl2), 8.5 br. s
(2H, N+H, OH). 31P NMR spectrum: δP 20.5 ppm.
О,O-Dioctyl (1-hydroxy-3-diethylamino-2,2-di-
methylpropyl)phosphonate (IIIb) was prepared
analogously from 2.5 g (16 mmol) of 3-diethylamino-
2,2-dimethylpropanal Ia and 4.87 g (16 mmol) of
(3-Hydroxy-3-O,O-dihexylphosphoryl-2,2-dimethyl-
propyl)ethylammonium dichloroethanoate (Vc) was
obtained similarly from 2 g (5 mmol) of О,О-dihexyl
(1-hydroxy-3-ethylamino-2,2-dimethylpropyl)phosphonate
IIIc and 0.68 g (5 mmol) of dichloroacetic acid IV.
Yield 2.5 g (94.3%). IR spectrum, ν, cm–1: 1062 (Р–О–С),
1213 (Р=О), 1650 (С=О), 2500, 2673 (N+H2), 3120
(ОН). 1H NMR spectrum [(СD3)2СО], δ, ppm: 0.8–1.9
m (31H, 2C5H11, NCH2Ме, CMe2), 3.2 m (4H,
МеСН2N+H2CH2), 4.15 m (5H, 2OCH2, PCH), 5.9 s
(1H, CHCl2), 7.0 br.s (3H, N+H2, OH). 31P NMR spec-
trum: δP 24.47 ppm. Found, %: N 2.84; P 5.95; Cl
14.00. C21H44NO6Cl2P. Calculated, %: N 2.75; P 6.09;
Cl 13.95
1
dioctylphosphorous acid IIb. Yield 7 g (95%). H
NMR spectrum (CDCl3), δ, ppm: 0.6–1.7 m (42H,
2C7H15, 2NCH2Ме, CMе2), 2.55 m (6H, NCH2,
2NCH2Me), 3.8 m (6H, 2OCH2, PCH, ОН). 31P NMR
spectrum: δP 24.5 ppm.
О,O-Dihexyl (1-hydroxy-3-ethylamino-2,2-dimethyl-
propyl)phosphonate (IIIc) was prepared analogously
from 5 g (39 mmol) of 3-ethylamino-2,2-dimethyl-
propanal Ib and 9.7 g (39 mmol) of dihexyl-
1
phosphorous acid IIa. Yield 13 g (88.4%). H NMR
spectrum [(СD3)2СО], δ, ppm: 0.8–1.8 m (31H,
2C5H11, NCH2Ме, CMe2), 2.75 m (4H, МеСН2·
NНCH2), 3.60 m (1Н, PCH), 4.05 m (4Н, 2OCH2), 5.4
О,О-Dihexyl [1-(benzoyloxy)-2,2-dimethyl-3-diethyl-
aminopropyl]phosphonate (VIIа). To a solution of
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SYNTHESIS AND ACYLATION OF O,O-DIHEXYL(DIOCTYL)-[1-HYDROXY-3-….
1339
1.2 g (3 mmol) of О,О-dihexyl (1-hydroxy-3-diethyl-
amino-2,2-dimethylpropyl)phosphonate IIIa and 0.304 g
(3 mmol) of triethylamine in 20 ml of anhydrous
diethyl ether under constant stirring at room tem-
perature was added a solution of 0.422 g (3 mmol) of
benzoyl chloride VIa in 5 ml of diethyl ether. The
reaction mixture was stirred at room temperature for
1 h. The precipitated triethylamine hydrochloride was
filtered off and washed with diethyl ether (5 ml). Then
the solvent and volatile components were removed in a
high vacuum. Yield 1.72 g (89.3%). 1H NMR spectrum
(CDCl3), δ, ppm: 0.6–1.6 m (34H, 2C5H11, 2NCH2Ме,
CMe2), 2.5 m (6H, NCH2, 2NCH2Ме), 3.90 m (4H,
kept overnight. The precipitated triethylamine hydro-
chloride was filtered off and washed with tetra-
hydrofuran (15 ml). Then the solvent and volatile
components were removed in a high vacuum. Yield
1
2.05 g (75%). H NMR spectrum (CDCl3), δ, ppm:
0.7–1.9 m (34H, 2C5H11, 2NCH2Ме, CМe2), 2.7 m
(6H, NCH2, 2NCH2Ме), 4.1 m (4H, 2OCH2), 5.5 d
2
(1H, PCH, JPH 10.0 Hz), 7.9 d, 8.8 d (4H, Py). 31P
NMR spectrum: δP 20.6 ppm.
О,О-Dioctyl [1-(4-azinecarbonyloxy)-3-diethyl-
amino-2,2-dimethylpropyl]phosphonate (VIId) was
prepared similarly from 2.5 g (5.4 mmol) of О,О-
dioctyl (1-hydroxy-3-diethylamino-2,2-dimethylpropyl)-
phosphonate IIIb and 0.96 g (5.4 mmol) of 4-(chloro-
2
2OCH2), 5.38 d (1H, PCH, JPH 11.1 Hz), 7.2–8.0 m
(5H, Ph). 31P NMR spectrum: δP 19.58 ppm. Found, %:
N 2.83; P 5.92. C30H52NO5P. Calculated, %: N 2.74; P
6.05.
1
carbonyl)azinium chloride VIb. Yield 2.6 g (80%). H
NMR spectrum (acetone-d6), δ, ppm: 0.8–1.8 m (42H,
2C7H15, 2NCH2Ме, CMe2), 2.5 m (6H, NCH2,
2NCH2Ме), 4.0 m (4H, 2OCH2), 5.4 d (1H, PCH, 2JPH
10.0 Hz), 7.8 d, 8.75 d (4H, Py). 31P NMR spectrum:
δP 20.1 ppm.
О,О-Dioctyl [1-(benzoyloxy)-2,2-dimethyl-3-diethyl-
aminopropyl]phosphonate (VIIb) was prepared
similarly from 1.05 g (2.3 mmol) of О,О-dioctyl (1-
hydroxy-3-diethylamino-2,2-dimethylpropyl)phos-
phonate IIIb and 0.32 g (2.3 mmol) of benzoyl
О,О-Dihexyl [3-(4-azinecarbonylamino)-1-hydroxy-
2,2-dimethylpropyl]phosphonate (VIIIb). To
a
1
chloride VIа. Yield 1.1 g (85.5%). H NMR spectrum
solution of 2 g (5 mmol) of О,О-dihexyl (1-hydroxy-3-
ethylamino-2,2-dimethylpropyl)phosphonate IIIc and
1.06 g (10.5 mmol) of triethylamine in 20 ml of
tetrahydrofuran under cooling to 0°C was added a
solution of 0.89 g (5 mmol) of 4-(chlorcarbonyl)
azinium chloride VIb in 10 ml of tetrahydrofuran. The
reaction mixture was warmed to room temperature and
left overnight. The precipitated triethylamine hydro-
chloride was filtered off and washed with tetra-
hydrofuran (10 ml). Then the solvent and volatile com-
ponents were removed in a high vacuum. Yield 2.1 g
(70%). 1H NMR spectrum (CDCl3), δ, ppm: 0.8–1.9 m
(31H, 2C5H11, NCH2Ме, CМe2), 2.8–3.4 m (5H,
МеСН2NCH2, PCH), 4.1 m (4H, 2OCH2), 7.8 d, 8.6 d
(4H, Py), 8.2 br.s (1Н, ОН). 31P NMR spectrum: δP
23.27 ppm. Found, %: N 5.43; P 6.18. C27H45N2O5P.
Calculated, %: N 5.50; P 6.09.
(CDCl3), δ, ppm: 0.8–1.8 m (42H, 2C7H15, 2NCH2Ме,
CMе2), 2.7 m (6H, NCH2, 2NCH2Ме), 4.0 m (4H,
2
2OCH2), 5.45 d (1H, PCH, JPH 11.0 Hz), 7.35– 8.2 m
(5H, Ph). 31P NMR spectrum: δP 24.8 ppm.
О,О-Dihexyl [3-(benzoylethylamino)-1-hydroxy-
2,2-dimethylpropyl]phosphonate (VIIIа) was prepared
similarly from 2.5 g (6.6 mmol) of О,О-dihexyl (1-
hydroxy-3-ethylamino-2,2-dimethylpropyl)phosphonate
IIIc, 0.67 g (6.6 mmol) of triethylamine in 20 ml of
anhydrous diethyl ether, and 0.93 g (6.6 mmol) of
benzoyl chloride VIa in 10 ml of diethyl ether. Yield
1
2.7 g (80%). H NMR spectrum [(СD3)2СО], δ, ppm:
0.8–1.8 m (31H, 2C5H11, NCH2Ме, CMe2), 3.6 m (4H,
МеСН2NCH2), 4.1 m (5H, 2OCH2, PCH), 7.5 s (5H,
Ph). 31P NMR spectrum: δP 24.66 ppm. Found, %: N
2.81; P 6.02. C28H46NO5P. Calculated, %: N 2.76; P
6.10.
O,О-Dihexyl [3-(benzoylethylamino)-1-(benzoyl-
oxy)-2,2-dimethylpropyl]phosphonate (IX). To a
solution of 2 g (5 mmol) of О,О-dihexyl (1-hydroxy-3-
ethylamino-2,2-dimethylpropyl)phosphonate IIIc and
1.06 g (10.5 mmol) of triethylamine in 20 ml of
anhydrous ether at room temperature was added drop-
wise a solution of 1.4 g (10 mmol) of benzoyl chloride
VIa in 10 ml of diethyl ether. The reaction mixture
was heated on a water bath for 5–6 h. The precipitated
triethylamine hydrochloride was filtered off and
О,О-Dihexyl [1-(4-azinecarbonyloxy)-3-diethyl-
amino-2,2-dimethylpropyl]phosphonate (VIIc). To a
solution of 2 g (5 mmol) of О,О-dihexyl (1-hydroxy-3-
diethylamino-2,2-dimethylpropyl)phosphonate
IIIa
and 1.06 g (10.3 mmol) of triethylamine in 20 ml of
tetrahydrofuran under cooling and stirring was added a
solution of 0.9 g (5 mmol) of 4-(chlorocarbonyl)-
azinium chloride VIb in 10 ml of tetrahydrofuran. The
reaction mixture was warmed to room temperature and
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1340
GAZIZOV et al.
washed with ether (10 ml). Then the solvent and
volatile components were removed in a high vacuum.
spectrum: δP 24.5 ppm. Found, %: N 3.13; P 6.49.
C23H46NO6P. Calculated, %: N 3.02; P 6.68.
1
Yield 1.9 g (56%). H NMR spectrum [(СD3)2СО], δ,
REFERENCES
ppm: 0.8–1.8 m (31H, 2C5H11, NCH2Ме, CМe2), 3.5
m (4H, МеСН2NCH2), 4.1 m (4H, 2OCH2), 5.35 d,
5.55 d (1Н, PCH, 2JPH 11.5 Hz), 7.4–8.2 m (10H, 2Ph).
31P NMR spectrum: δP 25.3 ppm. Found, %: N 2.41; P
4.92. C35H50NO6P. Calculated, %: N 2.29; P 5.06.
1. Gazizov, M.B., Khairullin, R.A., Bagauva, L.R.,
Sinyashin, O.G., Gaisin, L.G., Karimova, R.F., and
Shaikhutdinov, R.M., Russ. J. Gen. Chem., 2003,
vol. 73, no. 9, p. 1579.
2. Dyatlova, N.M., Temnikova, V.Ya., and Popov, K.I.,
Kompleksony i kompleksonaty metallov (Metal Chela-
tors and Complexonates), Moscow: Khimiya, 1988,
p. 544.
О,О-Dihexyl
[-2,2-dimethyl-3-(ethanoylethyl-
amino)-1-acetoxypropyl]phosphonate (XI). To 1.5 g
(4 mmol) of О,О-dihexyl (1-hydroxy-3-ethylamino-
2,2-dimethylpropyl)phosphonate IIIc with stirring was
added dropwise 1.02 g (10 mmol) of acetic anhydride
(X). The reaction mixture was heated at a bath
temperature of 80–90°C for 8 h. Then the volatiles
were removed in a high vacuum. Yield 1.3 g (77.4%).
1H NMR spectrum [(СD3)2СО], δ, ppm: 0.8–1.8 m
(31H, 2C5H11, NCH2Ме, CМe2), 2.0 s, 2.1 s [6H,
CH3С(О)], 3.5 m (4Н, МеСН2NCH2), 4.1 m (4Н,
3. Pudovik, A.N., Gur’yanova, I.V., and Ishmaeva, E.A.,
Reaktsii
i
metody issledovaniya organicheskikh
soedinenii, 1968, vol. 19, p. 11.
4. Kazitsyna,, L.A. and Kupletskaya, I.B., Primenenie UF,
IK- i YaMR-spektroskopii v organicheskoi khimii
(Application of UV, IR, and NMR Spectroscopy in
Organic Chemistry), Moscow: Vysshaya Shkola, 1971,
p. 264.
2
2OCH2), 5.1 d (1Н, PCH, JPH 11.5 Hz). 31P NMR
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 7 2013