Reaction of dialkylphosphites with N-alkyl-2-chloraldimines

Article abstract of DOI:10.1134/S1070363210120042

Reactions of some dialkylphosphorous acids with the N-substituted 2-chloroimines were studied. It was shown that the nature of substituents at the nitrogen and phosphorus atoms in the starting materials affected the structure of the reaction products. Pleiades Publishing, Ltd., 2010.

Full text of DOI:10.1134/S1070363210120042

ISSN 1070-3632, Russian Journal of General Chemistry, 2010, Vol. 80, No. 12, pp. 2425–2429. © Pleiades Publishing, Ltd., 2010.
Original Russian Text © M.B. Gazizov, R.A. Khairullin, A.A. Minnikhanova, A.I. Alekhina, A.A. Bashkirtsev, O.G. Sinyashin, 2010, published in Zhurnal
Obshchei Khimii, 2010, Vol. 80, No. 12, pp. 1963–1967.
Reaction of Dialkylphosphites with N-Alkyl-2-chloraldimines
M. B. Gazizova, R. A. Khairullina, A. A. Minnikhanovaa,
A. I. Alekhinaa, A. A. Bashkirtseva, and O. G. Sinyashinb
a Kazan State Technological University,
ul. K. Marksa, 68, Kazan, Tatarstan, 420015 Russia
e-mail: mukattisg@mail.ru
b Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Centre,
Russian Academy of Sciences, Kazan, Tatarstan, Russia
Received February 18, 2010
Abstract―Reactions of some dialkylphosphorous acids with the N-substituted 2-chloroimines were studied. It
was shown that the nature of substituents at the nitrogen and phosphorus atoms in the starting materials affected
the structure of the reaction products.
DOI: 10.1134/S1070363210120042
Among the organophosphorus compounds the
compounds containing aminoalkylphosphoryl
fragments are of a great practical and theoretical
interest. These compounds possess a wide spectrum of
useful properties. One of the basic approaches to the
synthesis of aminoalkyl phosphonates is the addition
of dialkyl phosphites to imines.
types of polyfunctional organophosphorus compounds
we studied the reaction of dimethyl-, diethyl, diisopro-
pyl-, dibutyl-, di-(2-chloroethyl)phosphorous acids I
with 2-chloroimines II containing either tert-butyl, or
isopropyl, or benzyl substituent at the nitrogen atom.
The reaction of acids I with compounds II occurs
through the initial formation of adducts, whose
phosphorus nuclei resonate at 26–29 ppm. When R2 =
t-Bu and R1 = Me, the adduct III is crystalline and
undergoes no changes at the long storage.
We have shown earlier [1] that 2-halo-substituted
imines react with dialkyl phosphites to form new types
of the organophosphorus compounds along with
adducts. The structure of the end products was found
to depend on the halogen nature.
When the reaction mixture was kept for 15–20 days,
the initial adduct underwent further transformations,
therewith the structure of the reaction product
depended on the nature of substituents at the P(IV) and
N atoms. Thus, the ease of the transformation and the
Aiming to understand the influence of the nature of
substituents at the atoms P(IV) and N(III) on the
structure of the formed products and to synthesize new
Cl
Cl
(R1O)2P(O)H + Me2CCH=NR2
(R1O)2P(O)CH_CMe2
NHR2
I
II
III
(R1O)2P(O)
(R1O) P(O)
CMe2
CMe2
NHR2
CH
CH
Cl
2
Cl_
IV
+
NHR2
V
I, R1 = Me (a), Et (b), i-Pr (c), Bu (d), ClCH2CH2 (e); II, R2 = t-Bu (а), Bz (b), i-Pr (c); III, R1 = Me, R2 = t-Bu (а); R1 = Et,
R2 = t-Bu (b); R1 = ClCH2CH2, R2 = t-Bu (c); R1 = Me, R2 = Bz (d); R1 = i-Pr, R2 = Bz (e); R1 = Bu, R2 = Bz (f); R1 = ClCH2CH2, R2 =
Bz (g); R1 = ClCH2CH2, R2 = i-Pr (h).
2425

2426
GAZIZOV et al.
Cl
CMe2 + (R1O)2P(O)CH CMe2
(R1O)2P(O)CH
_
+
ClR2
2
:
N
H
NHR
V
IV
(R1O)2P(O)CH
CMe2 + (R1O)2P(O)CH CMe2
+NH2R2Cl_
Cl
VI
NR2
VII
VI, R1 = i-Pr, R2 = Bz (а); R1 = Bu, R2 = Bz (b); R1 = ClCH2CH2, R2 = Bz (c); R1 = ClCH2CH2, R2 = i-Pr (d); VII, R1 = Me,
R2 = t-Bu (а); R1 = Me, R2 = Bz (b); R1 = i-Pr, R2 = Bz (c); R1 = Bu, R2 = Bz (d); R1 = ClCH2CH2, R2 = Bz (e); R1 =
ClCH2CH2, R2 = i-Pr (f).
adduct structure depend on the substituent nature at the
atom N(III): when R2 = i-Pr or Bz, the further
transformation of the adduct proceeds considerably
more easily than with R2 = t-Bu. Probably, in the last
case the cyclic intermediate IV is formed more dif-
ficulty than in the case when R2 = i-Pr and Bz because
of the steric hindrances.
aminoalkyl phosphonate hydrochloride VI and aziri-
dine-2-phosphonate VII, respectively. After treating
the reaction mixture with diethyl ether the crystalline
salt VI was isolated. Compound VII with a small ad-
mixture of the adduct III was isolated from the ether
solution.
The stability of salt VI depends on the substituent
nature at the atom P(IV): if R1 = ClCH2CH2 and R2 =
i-Pr or Bz the salt is stable; if R1 = Ме, it transforms
into betaine IX.
The reaction of di(2-chloroethyl)phosphorous acid
with 2-chloroimine containing isopropyl or benzyl
substituent at the nitrogen atom gives rise to 2-
Cl
Cl
P+ CH CMe2
OH
MeO
CH
H
CMe2
Me
(MeO)2
P
O
+NHR2Cl_
Cl_
NHR2
O
VI
Cl
O
O
Cl
CH CMe2
MeOP
MeOP
CH CMe2
2
_MeCl
:
NHR
_O
+NH2R2
IX
O
H
VIII
IX, R2 = t-Bu (а); R2 = Bz (b).
The structure of the compounds obtained is
100 instrument (36.5 MHz) relative to external 85%
Н3РО4.
1
confirmed by the elemental analysis and Н, 31Р, 13С
NMR spectroscopy data.
Reaction of N-(2-methyl-2-chloropropylidene)-
tert-butylamine IIa with dimethylphosphorous acid
Ia. а. Compound Iа (12.98 g) and imine IIа (19.07 g)
were mixed under argon. Slight warming up of the
reaction mixture was observed. The mixture was kept
for 24 h at room temperature. On the dissolution of the
EXPERIMENTAL
1
The Н NMR spectra were registered on a Tesla
BW-567 spectrometer (100 MHz) relative to internal
TMS. The 31Р NMR spectra were recorded on a СХР-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 12 2010

2427
REACTION OF DIALKYLPHOSPHITES WITH N-ALKYL-2-CHLORALDIMINES
reaction mixture in ether a turbid solution was obtained
cleared by filtration. The precipitate on the filter
contained the second reaction product IXa, which
formed in a great quantity at the prolonged keeping the
reaction mixture (see method b). After the removal of
diethyl ether we obtained 26.51 g (83%) of dimethyl
(1-tert-butylamino-2-methyl-2-chloropropyl)phospho-
prepared similarly from 13.05 g of compound Ie and
16.73 g of imine IIа. Yield 25.01 g (84%) of crude
1
product. Н NMR spectrum (CDCl3), δ, ppm: 1.03 s
(9H, CMe3), 1.54 s and 1.64 s (6H, CMe2), 1.58–1.62
2
br.s (1H, NH), 3.1 d (1Н, РСН, JРH 18.5 Hz), 3.6 m
(4Н, CH2Cl), 4.19 m (4Н, CH2OP). 31Р NMR spectrum
(СНСl3): δP 27.1 ppm.
1
nate IIIa, mp 76°С. Н NMR spectrum (CDCl3) δ,
Reaction of N-(2-methyl-2-chloropropylidene)-
benzylamine IIb with dimethylphosphorous acid Ia.
а. To 8.47 g of compound Iа was dropwise added
15.1 g of imine IIb at the stirring under argon. The
reaction mixture was warmed up to 30ºС. After stirring
for 24 h at room temperature and removal of volatile
products we obtained 22.2 g (94%) of crude dimethyl-
(1-benzylamino-2-methyl-2-chloropropyl)phosphonate
ppm: 1.29 s (9Н, СМе3), 1.83 s and 1.90 s (6Н, СМе2),
2
1.82–1.87 br.s (1Н, NH), 3.37 d (1Н, РСН, JРН 20
Hz), 3.93 d and 3.94 d [6Н, Р(ОМе)2, 3JРН 11 Hz]. 31Р
NMR spectrum (ССl4): δP 29.3 ppm.
b. Compound Iа (4.4 g) and imine IIа (6.53 g) were
mixed under argon. Slight warming up of the reaction
mixture was observed. The mixture was kept for 30–
35 days at room temperature, then treated with diethyl
ether and filtered. The crystals precipitated were
separated and dried in a vacuum. Yield 4.3 g (45%) of
methyl (2-tert-butylammonio-2-methyl-1-chloro-
1
IIId. Н NMR spectrum (СDCl3), δ, ppm: 1.69 s and
1.70 s (6H, CMe2), 1.85 br.s (1Н, NH), 2.29 d and 3.74
2
d (1Н, РСН, JРH 16.2 Hz), 3.73 d and 3.78 d (6Н,
3
2МеO, JРH 10.6 Hz), 4.00 d and 3.85 d (2Н, СН2Ph,
1
propyl)phosphonate IXa, mp 150–151°C. Н NMR
2JHH 12.6 Hz), 7.17-7.29 m (5Н, Ph). 31Р NMR
spectrum (СНCl3): δP 25.5 ppm.
spectrum (CDCl3), δ, ppm: 1.63 s (9Н, СМе3), 1.71 s
4
and 1.80 d (6Н, СМе2, JРН 0, 2.3 Hz), 4.61 d (1Н,
2
3
РСН, JРН 9 Hz), 3.93 d (3H, РОМе, JРН 10 Hz), 9.6
b. Compound Iа (8.47 g) and imine IIb (15.1 g)
were mixed under argon. Slight warming up of the
reaction mixture was observed. The mixture was kept
for 30–35 days at room temperature. During this time
the reaction mixture was treated with diethyl ether 5
times. The precipitated crystals were filtered off and
dried in a vacuum. The mother liquor was concentrated
and kept at room temperature before the next dilution
with ether. Yield of methyl (2-benzylammonio-2-
methyl-1-chloropropyl)phosphonate IXb is 11.2 g
br.d and 10.9 br.d (2Н, NH2). 31Р NMR spectrum
(CНCl3): δP 11.32 ppm.
+
According to the 31Р and Н NMR spectral data,
1
the residue (5.4 g) is a mixture of the adduct IIIa [δP
28.8 ppm (CCl4)] and dimethyl (1-tert-butylamino-3,3-
dimethylaziridin-2-yl)phosphonate VIIa [δP 26.5 ppm
(CCl4)] in the ratio 2:1.
Reaction of N-(2-methyl-2-chloropropylidene)-
tert-butylamine IIa with diethylphosphorous acid
Ib. Compound Ib (5.52 g) and imine IIа (6.8 g) were
mixed under argon. The reaction mixture was warmed
up to 31ºС. The mixture was kept at room temperature
for 24 h, and then treated with diethyl ether, filtered,
and concentrated. Yield of diethyl (1-tert-butylamino-
2-methyl-2-chloropropyl)phosphonate IIIb is 19.7 g
(81%). It was identified unpurified due to its thermal
1
(63%), mp 161–163°С. Н NMR spectrum (СD3OD),
δ, ppm: 1.65 s and 1.67 s (6H, CMe2), 3.74 d (3Н,
МеOP, 3JРH 10.3 Hz), 4.22 d (1Н, РСН, 2JРH 10.6 Hz),
2
4.23 d and 4.29 d (2Н, СН2Ph, JHH 12.6 Hz), 7.44–
7.56 m (5Н, Ph), 9.5 br.s (2Н, +NH2). 31Р NMR
spectrum (СН3ОН): δP 13.6 ppm. Found, %: N 5.0; Cl
11.85; Р 10.45. С12Н19NClPO3. Calculated, %: N 4.60;
Cl 12.00; Р 10.10.
1
lability. Н NMR spectrum (CDCl3), δ, ppm: 1.08 s
3
(9Н, СМе3), 1.28 t (6Н, РОСН2Ме, JНН 7 Hz), 1.28–
After the removal of diethyl ether from the mother
liquor the residue (7.44 g) consists of dimethyl (1-
benzyl-3,3-dimethylaziridin-2-yl)phosphonate VIIа of
1.44 br.s (1Н, NH), 1.60 s and 1.64 s (6Н, СМе2), 3.03
2
d (1Н, РСН, JРН 19 Hz), 4.05 quintet (4Н, РОСН2,
3JНН= 3JРН 7 Hz). 31Р NMR spectrum (CDCl3): δP 26.43
1
90% purity. Н NMR spectrum (CDCl3), δ, ppm: 1.45
ppm.
d (1Н, РСН, 3JРH 18 Hz), 1.33 d and 1.42 s (6H, CMe2,
4JРH 2.5 Hz), 3.7 d (2H, CH2Ph, 4JРH 3.2 Hz), 3.64 d
and 3.51 d (6Н, 2 МеО, 3JРH 10.7 Hz), 7.2-7.4 m (5 Н,
Ph). 31Р NMR spectrum (СН3ОН), δP, ppm: 24.9
(90%); 18.3 (3%); 10.5 (7%).
Reaction of N-(2-methyl-2-chloropropylidene)-
tert-butylamine IIa with di(2-chloroethyl)phos-
phorous acid Ie. Di(2-chloroethyl) [1-tert-butyl-
amino-2-methyl-2-chloropropyl]phosphonate IIIc was
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 12 2010

2428
GAZIZOV et al.
Reaction of N-(2-methyl-2-chloropropylidene)
Dibutyl (2-benzylamino-2-methyl-1-chloropropyl)
phosphonate hydrochloride VIb was prepared
similarly from 5.95 g of compound Id and 6.01 g of
benzylamine IIb with diisopropylphosphorous acid
Ic. Compound Ic (2.82 g) and imine IIb (15.1 g) were
mixed under argon. Slight warming up of the reaction
mixture was observed. The mixture was kept for
60 days at room temperature. During this time the
reaction mixture was treated with diethyl ether 4 times,
and the reaction product, diisopropyl (2-benzylamino-
2-methyl-1-chloropropyl)phosphonate hydrochloride
1
imine IIb. Yield 3.27 g (27%), mp 122°C. Н NMR
spectrum (СDСl3), δ, ppm: 0.945 t and 0.950 t (6Н, 2
3
CH2CH3, JНH 7.0 Hz), 1.69 quintet (4Н, 2 CH2CH2,
3JНH 7.0 Hz), 1.43 m (4Н, 2 ОCH2CH2), 1.63 s and
1.82 s (6Н, CМе2), 4.03 d and the second doubled is
overlapped with the signals of РОСН2-group (2Н,
1
2
VIa,was isolated. Yield 1.9 g (21%), mp 145°C. Н
CH2Рh, JНH 12.7 Hz), 4.19–4.35 m (4Н, 2СН2ОР),
2
NMR spectrum (СDCl3), δ, ppm: 1.36 d and 1.38 d
5.25 d (1 Н, РСН, JРH 10 Hz), 7.42–7.58 m (5Н, Рh),
(6Н, CH31CH23СН5ОР, JH H
1
5
= JH H 6.0 Hz), 1.38 d
11.9 br.s and 8.9 br.s (2Н, NH2). 31Р NMR spectrum
3
3
2
5
+
and 1.43 d (6Н, CH33CH34CH6OP, JH H
3
6
=
3JH H
4
6
(СНСl3): δP 17.91 ppm. Found, %: N 3.65; Cl 16.90; Р
7.40. С17Н34NCl2PO3. Calculated, %: N 3.30; Cl 16.70;
Р 7.30.
3
6.1 Hz), 1.6 s and 1.82 s (6Н, CМе2), 4.01 d and 4.29 d
2
(2Н, CH2, JНH 12.7 Hz), 4.83 sextet (1Н, РОСН5·
CH31CH23, JPH
5
= JH H
1
5
= JH 3H = 6.0 Hz), 4.98 sextet
2
5
3
3
3
According to the 31Р and 1Н NMR spectral data, the
residue (5.55 g) is a mixture of the adduct IIIe (δР
23.3 ppm) and of dibutyl (1-benzyl-3,3-dimethyl-
aziridin-2-yl)phosphonate VIId (δР 22.5 ppm) in the
ratio 3:1.
(1Н, РОСН6CH33CH34, JPH
6
= JH H
3
6
= JH H = 6.0 Hz),
4
6
3
3
5.18 d (1Н, РСН, 2JРH 9.5 Hz), 8.84 br.s and 12.04 br.s
+
(2Н, NH2). 31Р NMR spectrum (СНСl3): δP 16.29
ppm. Found, %: N 3.65; Cl 17.50; Р 7.45.
С17Н30NCl2PO3. Calculated, %: N 3.50; Cl 17.80; Р
7.80.
According to the 31Р and 1Н NMR spectral data, the
residue (4.05 g) is a mixture of compounds IIIe and
VIIc in the ratio 3:1.
Reaction of N-(2-methyl-2-chloropropylidene)-
benzylamine IIb with di(2-chloroethyl)phosphorous
acid Ie. Di(2-chloroethyl) (2-benzylamino-2-methyl-1-
chloropropyl)phosphonate hydrochloride VIc was
prepared similarly from 13.35 g of compound Ie and
14.14 g of imine IIb. Yield 13.34 г (45%), mp 152–
153°C. 1Н NMR spectrum (CDCl3), δ, ppm: 1.67 s and
1.81 s (6H, CMe2), 3. 76 s (4Н, CH2OP), 4.50 m and
4.59 m (4Н, CH2Cl), 4.02 d and 4.29 d (2Н, СН2Ph,
O,O-Diisopropyl (1-benzylamino-2-methyl-2-
1
chloropropyl)phosphonate(IIIe). Н NMR spectrum
(СDCl3), δ, ppm: 1.29 d and 1.32 d (6Н, CH31CH32·
3
3
СН5ОР, JH H
1
5
= JH H 6.3 Hz), 1.32 d and 1.34 d (6Н,
2
5
CH33CH34CH6OP, JH H
3
6
= JH H 6.3 Hz), 1.75 s and
4
6
3
3
2
2JHH 12.3 Hz), 5.5 d (1Н, РСН, JРH 9 Hz), 7.28–7.57
+
m (5Н, Ph), 8.5 br.s and 12.1 br.s (2Н, NH2). 31Р
1.71 s (6Н, СМе2), 2.1 br.s (1Н, NH), 2.93 d (1Н,
2
РСН, JРH 17.34 Hz), 4.10 d and 4.89 d (2Н, CH2Ph,
NMR spectrum (CDCl3): δP 18.7 ppm. Found, %: N
3.25; Cl 32.00; Р 7.05. С15Н24NCl4PO3. Calculated, %:
N 3.00; Cl 32.25; Р 6.70.
2JНH 12.3 Hz), 4.75 heptet (1Н, РОСН5СН31СН32,
3JРH
5
=
3JН H
1
5
=
3JН H
6.3 Hz), 4.78 heptet (1Н,
3 3
2
5
РОСН6СН33СН34, JРH6 = JН H
3
6
= JН H 6.3 Hz), 7.28–
4
6
3
According to the 31Р and 1Н NMR spectral data, the
residue (5.95 g, 21%) is a mixture of compounds IIIg
and VIIe in the ratio 1:4.
7.38 m (5Н, Ph); 31Р NMR spectrum: δP 16.29 ppm.
O,O-Diisopropyl (1-benzyl-3,3-dimethylaziridin-
2-yl)phosphonate (VIIc). 1Н NMR spectrum (СDCl3),
4
O,O-Di(2-chloroethyl) (2-benzylamino-2-methyl-
δ, ppm: 1.25 d and 1.24 s (6Н, СМе2, JРH 3 Hz), 1.44
1
2
1-chloropropyl)phosphonate (IIIg). Н NMR spec-
d (1Н, РСН, JРH 17.3 Hz), 3.64 d and 3.74 d (2Н,
2
CH2Ph, JНH 14.2 Hz), 4.59 heptet (1Н, РОСН5·
trum (СDCl3), δ, ppm: 1.75 s and 1.76 s (6 Н, CMe2),
3.08 d (1Н, РСН, 2JРH 16.3 Hz), 7.10–7.26 m (5Н, Ph);
31Р NMR spectrum: δP 24.5 ppm.
СН31СН32, JРH
5
= JН H
1
5
3
= JН H 6.0 Hz), 4.61 heptet
2
5
3
3
3
(1Н, РОСН6СН33СН34, JРH
6
= JН H
3
6
= JН H 6.0 Hz),
4
6
3 3
1.24 d and 1.26 d, (6Н, CH31CH32СН5ОР, JH H
1
5
=
3
O,O-Di(2-chloroethyl) (1-benzyl-3,3-dimethylazi-
3
4
3JH H
3JH H
2
5
6.0 Hz), 1.29 d, 1.31 d (6Н, CH3 CH3 CH6OP,
1
ridin-2-yl)phosphonate (VIIe). Н NMR spectrum
3
3
6
= JH H
4
6
6 Hz), 7.20–7.26 m (5Н, Ph); 31Р NMR
(СDCl3), δ, ppm: 1.21 s and 1.32 s (6H, CMe2), 1.47 m
spectrum: δP 22.3ppm.
2
(1Н, РСН, JРH 18.9 Hz), 3.44 d and 3.67 d (2Н,
СН2Ph, 2JHH 13.5 Hz), 7.16-7.24 m (5Н, Ph); 31Р NMR
spectrum: δP 25.6 ppm.
Reaction of N-(2-methyl-2-chloropropylidene)
benzylamine IIb with dibutylphosphorous acid Id.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 12 2010

2429
REACTION OF DIALKYLPHOSPHITES WITH N-ALKYL-2-CHLORALDIMINES
Reaction of N-(2-methyl-2-chloropropylidene)iso-
propylamine IIc with di(2-chloroethyl)phosphorous
acid Ie. Compound Ie (20.14 g) and imine IIc
(14.35 g) were mixed under argon. Slight warming up
of the reaction mixture was observed. The mixture was
kept for 3 weeks at room temperature. During this time
the reaction mixture was treated with diethyl ether
5 times, and the reaction product, O,O-di(2-chloroethyl)
(2-isopropylamino-2-methyl-1-chloropropyl)phos-
phonate hydrochloride VId, was isolated. Yield 18.2 g
O,O-Di(2-chloroethyl) (2-isopropylamino-2-methyl-
1
1-chloropropyl)phosphonate (IIIh). Н NMR spec-
trum (СDCl3), δ, ppm: 1.75 s and 1.76 s (6Н, СМе2),
3.08 d (1Н, РСН, 2JРH 16.3 Hz); 31Р NMR spectrum: δP
25.9 ppm.
O,O-Di(2-chloroethyl) (1-isopropyl-3,3-dimethyl-
1
aziridin-2-yl)phosphonate (VIIf). Н NMR spectrum
3
(СDCl3), δ, ppm: 1.08 d and 1.14 d (6H, CНMe2, JHH
2
7.0 Hz); 1.38 s (6Н, CМе2); 1.43 d (1Н, РСН, JРH
1
(53%), mp 101°С. Н NMR spectrum (CDCl3), δ,
18 Hz), 2.3 m (1H, CНMe2), 3.68 m (4Н, СН2О), 4.35
ppm: 1.88 d (6H, CMe2), 1.58 d and 1.82 d (6H,
CНMe2, 3JHH 7.0 Hz), 2.3 m (1H, CНMe2), 3.9 m (4Н,
CH2OP), 4.7 m (4Н, CH2Cl), 5.85 d (1Н, РСН, 2JРH 13
31
m (4Н, СН2Сl); Р NMR spectrum: δP 25.6 ppm. The
mixture was identified in the unpurified form due to its
thermal lability.
+
Hz), 8.3 br. d and 11.2 br.s (2Н, NH2). 31 Р NMR
spectrum (СНСl3): δP 18.89 ppm. Found, %: N 3.62;
Cl 38.25; Р 8.58. С11Н24NCl4PO3. Calculated, %: N
3.82; Cl 38.65; Р 8.44.
According to the 31Р and 1Н NMR spectral data, the
residue (11.93 g) is a mixture of compounds IIIh and
VIIf in the ratio 1:4.
REFERENCES
1. Gazizov, M.B., Khairullin, R.A., Alekhina, A.A.,
Litvinov, I.A., Krivolapov, D.B., Latypov, Sh.K.,
Balandina, A.A., Musin, R., and Sinyashin, O.G.,
Mendeleev Commun. 2008, vol. 18, no. 5, p. 262.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 80 No. 12 2010