Polyfluoroalkyl Phosphates Bearing Propargyl Substituents

Article abstract of DOI:10.1134/S107036321904011X

Polyfluoroalkyl dichlorophosphates react easily with propargyl alcohol under mild conditions (22–62°С, 3 h, pyridine-toluene) to form previously unknown bis(2-propynyl) polyfluoroalkyl phosphates with a yield of 36–41%, a triple bond in which is capable of participating in the azide-alkyne cycloaddition reaction.

Full text of DOI:10.1134/S107036321904011X

ISSN 1070-3632, Russian Journal of General Chemistry, 2019, Vol. 89, No. 4, pp. 708–712. © Pleiades Publishing, Ltd., 2019.
Russian Text © The Authors(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 4, pp. 574–579.
Polyfluoroalkyl Phosphates Bearing Propargyl Substituents
S. I. Verkhoturovaa, A. M. Nalibaevab, S. N. Arbuzovaa, T. I. Kazantsevaa, S.V. Zinchenkoa,
V. L. Mikhailenkoc, N. A. Chernyshevaa, G. K. Bishimbaevab,
N. K. Gusarovaa, and B. A. Trofimova*
a A.E. Favorskii Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
*e-mail: boris_trofimov@irioch.irk.ru
b D.V. Sokolsky Institute of Fuel, Catalysis and Electrochemistry, Almaty, Kazakhstan
c Irkutsk State University, Irkutsk, Russia
Received December 29, 2018; revised December 29, 2018; accepted January 11, 2019
Abstract—Polyfluoroalkyl dichlorophosphates react easily with propargyl alcohol under mild conditions (22‒
62°С, 3 h, pyridine–toluene) to form previously unknown bis(2-propynyl) polyfluoroalkyl phosphates
with a yield of 36‒41%, a triple bond in which is capable of participating in the azide-alkyne cycloaddition
reaction.
Keywords: polyfluoroalkyl dichlorophosphates, alkyl dichlorophosphates, propargyl alcohol, bis(2-propynyl)
polyfluoroalkyl phosphates, bis(2-propynyl) alkyl phosphates, azide-alkyne cycloaddition reaction
DOI: 10.1134/S107036321904011X
In recent years, fluoroalkyl phosphates have
attracted increasing attention of researchers as effective
flame retardants (for example, non-combustible
electrolyte additives for Li-ion batteries [1–5]),
components for creating surface-active materials [6, 7],
and promising precursors for drug design [8–11]. The
introduction of additional reactive groups into a
fluoroalkyl phosphate molecule opens up new
possibilities for the widespread use of these
compounds in targeted organic synthesis. In this
regard, fluoroalkyl phosphates with propargyl
substituents are promising objects, the triple bond in
which can further enter into various atom-economic
addition and cycloaddition reactions [12–14], in
particular, the azide-alkyne cycloaddition reaction [14,
15–18].
phosphates 1a, 1b in the 9‒10 ppm region and
appearance of the signals of the target bis(2-propynyl) -
polyfluoroalkyl phosphates 3a, 3b in the range of
–1‒0 ppm. The reaction proceeded at room
temperature for 2 h with conversion of the initial
fluoroalkyl dichlorophosphates 1a, 1b of 80%. To
achieve complete conversion, the reaction mixture was
additionally heated at 60–62°C for 1 h (Scheme 1).
Under optimized conditions (22‒62°С, 3 h, Py–
toluene system), the yield of phosphates 3а, 3b is close
to quantitative (31P NMR). However, isolation of
phosphates 3a and 3b from the reaction mixture, and
especially their purification by distillation in vacuum,
led to a significant decrease in the preparative yield
(up to 36–41%) of the target compounds due to their
significant resinification.
The selected conditions were also suitable for the
synthesis of bis(2-propynyl) ethyl and bis(2-propynyl)
propyl phosphates 3c and 3d from ethyl or propyl
dichlorophosphates 1c, 1d and propargyl alcohol
(preparative yield of compounds 3c and 3d reached 38
and 42%, respectively).
Herein, for the first time we reported the synthesis
of phosphates containing both fluoroalkyl and
propargyl groups. The synthesis was performed by
reacting 2,2,2-trifluoroethyl and 2,2,3,3-tetrafluoro-
propyl dichlorophosphates 1a and 1b with propargyl
alcohol 2 in a pyridine–toluene system. The reaction
progress was monitored by 31P NMR spectroscopy by dis-
appearance of the signals of the initial dichloro-
Using the example of dipropargyl phosphates 3a,
3b and 3d, preliminary results were obtained on the
708

709
POLYFLUOROALKYL PHOSPHATES BEARING PROPARGYL SUBSTITUENTS
Scheme 1.
O
O
O
Py/PhMe
O
22−62°C, 3 h
P
RFCH2OPCl2
+ 2 HC CCH2OH
.
−2Py HCl
O
1a, 1b
2
RF
3a, 3b
RF = CF3 (a), HCF2CF2 (b).
possibility of using the synthesized compounds in the
reaction of the azide-alkyne cycloaddition. So,
phosphates 3a, 3b, and 3d reacted with benzyl azide
generated in situ from sodium azide and benzyl
chloride as terminal diacetylenes to form bis(1-benzyl-
1H-1,2,3-triazol-4-yl) alkyl phosphates 4a, 4b and 4d.
The reaction proceeded at room temperature for 4 (3a,
3b) or 7 h (3d) using the typical CuSO4–sodium
ascorbate–Et3N [15, 16] catalytic system in aqueous
acetonitrile (Scheme 2). In the absence of triethyl-
amine, no reaction occurs. Structure of the synthesized
triazoles 4 was unambiguously proven by 1H, 13C, 15N,
dichloromethane or acetone) did not lead to the desired
result. Moreover, triazoles 4 in these solvents are
unstable and undergo transformations, possibly
polymerization, since wide unresolved signals appear
in the 1H and 31P NMR spectra.
Propargyl compounds (for example, propargyl ethers,
N-propargylpyrroles, N-propargylimidazole, N-propargyl-
1,2,4-triazole) are known to undergo prototropic
isomerization in the presence of strong bases (t-BuOK,
KOH–DMSO) at a temperature of 20‒45°С) [12]. At
the same time, it turned out that the synthesized
dipropargyl phosphates 3 (shown on the example of
compounds 3b and 3d) are stable when heated to 97‒
98°C for 3 h in the system t-BuOK (30 mol %)–DMSO-d6
31
19F and P NMR spectroscopy, including two-dimen-
sional NMR spectroscopy (COSY, HSQC, HMBC).
1
and do not undergo any changes according to H and
During this process, triethylammonium hydro-
chloride and triethylbenzylammonium chloride were
also formed. Attempts to purify the target compounds
4 from the indicated salts (flash chromatography on
Al2O3 or on silica gel, eluting with chloroform,
31P NMR spectroscopy data.
In summary, a convenient method was developed
for the synthesis of previously unknown poly-
fluoroalkyl phosphates with propargyl substituents
Scheme 2.
O
O
O
P
+ NaN3 + PhCH2Cl
O
R
3a, 3b, 3d
N2
N1
N3
N
N
O
Ph
O
CuSO4, Na ascorbate, Et3N, MeCN
O
Ph
N
P
4
−Et3N.HCl, −[PhCH2NEt3]Cl
5
O
R
4a, 4b, 4d
R = CF3 (a), HCF2CF2 (b), Et (d).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 4 2019

710
VERKHOTUROVA et al.
based on the reaction of polyfluoroalkyl dichlorophos-
phates with propargyl alcohol, which proceeds easily
in the pyridine–toluene system under mild conditions
(22‒62°C, 3 h). The synthesized compounds are
promising precursors of drugs, demanded components
for the design of innovative materials and reactive
building blocks for element organic synthesis.
Bis(2-propynyl) (2,2,2-trifluoroethyl) phosphate
(3a). Yield 4.2 g (41%), colorless liquid, bp 62‒64°C
(0.4 mmHg), d420 1.3470, nD20 1.4098. IR spectrum, ν,
cm–1: 3303 s, 3246 s, 3008 m, 2973 m, 2955 m, 2889
m, 2829 w, 2744 w, 2596 w, 2440 w, 2413 w, 2256 w,
2132 s, 1992 w, 1915 w, 1807 w, 1624 w, 1455 m,
1423 m, 1376 m, 1276 s, 1178 s, 1109 m, 1033 s, 994
1
m, 886 m, 777 m, 689 m, 658 m, 505 m. Н NMR
4
EXPERIMENTAL
spectrum (CDCl3), δ, ppm: 2.65 t (2H, CH≡, JHH
=
=
=
3
3
2.3 Hz), 4.41 qn (2H, CF3CH2, JHF = 8.0, JHP
13
15
19
31
1H, C, N, F, P NMR spectra were registered
on Bruker DPX 400 and Bruker AV-400 spectrometers
(400.13, 101.61, 40.55, 376.50 and 161.98 MHz,
respectively) relative to internal HMDS (1H, 13C),
MeNO2 (15N), CFCl3 (19F) or external 85% H3PO4
(31P). Two-dimensional homo- and heteronuclear
NMR spectroscopy methods (COSY, HSQC, HMBC)
were used to assign the signals in the 1H and 13C NMR
spectra. IR spectra were recorded on a Bruker IFS 25
spectrometer in a thin layer. Electron impact mass
spectra (70 eV) were taken on a GCMS-QP5050A
Shimadzu instrument.
3
4
8.0 Hz), 4.74 d. d (4H, ≡CCH2, JHP = 10.7, JHH
2.3 Hz). 13С NMR spectrum (CDCl3), δС, ppm: 56.0 d
(≡CCH2, 2JCP = 4.9 Hz), 63.8 q. d (CF3CH2, 2JCF = 38.2,
2JCP = 4.4 Hz), 76.6 d (C≡, 3JCP = 7.1 Hz), 76.9 (CH≡),
122.4 q. d (CF3, JCF = 277.6, JCP = 10.5 Hz). 19F
1
3
3
NMR spectrum (CDCl3), δF, ppm: –75.0 t (CF3, JHF
=
8.0 Hz). 31P NMR spectrum (CDCl3): δP –0.9 ppm.
Found, %: C 37.32; H 3.24; F 22.24; P 11.78.
C8H8F3O4P. Calculated, %: C 37.52; H 3.15; F 22.25;
P 12.09.
Bis(2-propynyl) (2,2,3,3-tetrafluoropropyl) phos-
phate (3b). Yield 4.1 g (36%), colorless liquid, bp 85‒
87°C (0.4 mmHg), d420 1.3802, nD20 1.4128. IR spec-
trum, ν, cm–1: 3305 s, 3246 m, 3005 w, 2964 w, 2889
w, 2853 w, 2440 w, 2132 w, 1984 w, 1913 w, 1806 w,
1657 w, 1455 w, 1414 w, 1376 w, 1286 s, 1237 m,
1213 m, 1189 m, 1109 m, 1034 s, 994 m, 949 m, 886
m, 833 m, 778 m, 733 m, 677 m, 647 m, 549 m, 510
The starting polyfluoroalkyl dichlorophosphates 1a,
1b were obtained from POCl3 and polyfluoroalkanols
in the presence of LiCl according to the known
procedure [10, 19]; alkyl dichlorophosphates 1c, 1d
were obtained according to the procedure [20].
General procedure for the synthesis of bis(2-
propynyl) alkyl phosphates 3a‒3d. To a solution of
dichlorophosphate 1 (0.04 mol) in 80 mL of toluene
was added dropwise with stirring a solution of
propargyl alcohol (0.08 mol, 4.49 g) and pyridine
(0.09 mol, 7.12 g) in 15 mL of toluene at room
temperature within 1 h. A white precipitate of pyridine
hydrochloride was formed. The reaction mixture was
stirred for another 1 h at room temperature and then for
another 1 h at 60‒62°C and kept overnight. The
organic layer was decanted and filtered, the toluene
from the filtrate was distilled off under reduced
pressure. The residue was dissolved in 30 mL of
dichloromethane. The precipitate (pyridine hydro-
chloride) remaining after decantation of the organic
layer was dissolved in 30 mL of water, the aqueous
solution was extracted with dichloromethane (5 × 20 mL).
The dichloromethane solutions were combined,
washed successively with a saturated aqueous solution
of NaHCO3 (5 × 20 mL) and water (5 × 20 mL), dried
over Na2SO4. Dichloromethane was distilled off under
reduced pressure, and the residue was distilled in
vacuum.
1
m. Н NMR spectrum (CDCl3), δ, ppm: 2.65 t (2H,
4
CH≡, JHH = 2.4 Hz), 4.43 t. d. t (2H, CF2CH2O, 3JHF
=
12.1, 3JHP = 7.0, 4JHF = 1.3 Hz), 4.74 d. d (4H, ≡CCH2O,
3JHP = 10.9, JHH = 2.4 Hz), 5.96 t. t (1H, CHF2, 2JHF
=
4
3
53.1, JHF = 4.3 Hz). 13С NMR spectrum (CDCl3), δС,
2
ppm: 56.0 d (≡CCH2O, JCP = 4.7 Hz), 63.4 t. d
2
2
(CF2CH2O, JCF = 30.2, JCP = 4.7 Hz), 76.4 d (C≡,
3JCP = 6.9 Hz), 77.0 (CH≡), 109.0 t. t (CHF2, JCF
=
1
250.4, 2JCF = 34.9 Hz), 113.7 t. t. d (CF2, 1JCF = 251.3,
2JCF = 27.3 Hz, JCP = 9.5 Hz). 19F NMR spectrum
3
2
(CDCl3), δF, ppm: –138.4 d (CHF2, JHF = 53.1 Hz),
–125.2 m (CF2). 31P NMR spectrum (CDCl3): δP
–0.8 ppm. Found, %: C 37.35; H 3.19; F 26.30; P
10.60. C9H9F4O4P. Calculated, %: C 37.52; H 3.15; F
26.37; P 10.75.
Bis(2-propynyl) ethyl phosphate (3c). Yield 3.1 g
(38%), colorless liquid, bp 85‒87°C (0.4 mmHg), d420
1.1560, nD20 1.4500 (nD20 1.4488 [21]). IR spectrum, ν,
cm–1: 3295 s, 3229 s, 2987 s, 2945 m, 2913 m, 2883 m,
2826 w, 2779 w, 2747 w, 2636 w, 2529 w, 2438 w,
2127 s, 2080 w, 2024 w, 1899 w, 1783 w, 1637 w,
1479 m, 1451 m, 1395 m, 1374 m, 1277 s, 1166 m,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 4 2019

711
POLYFLUOROALKYL PHOSPHATES BEARING PROPARGYL SUBSTITUENTS
1
1031 s, 995 s, 857 s, 851 s, 754 m, 688 m, 649 m, 560
m. Н NMR spectrum (CDCl3), δ, ppm: 1.32 t (3H,
identified by H and 15N NMR spectroscopy using
1
authentic samples).
3
4
Me, JHH = 7.1 Hz), 2.56 t (2H, CH≡, JHH = 2.4 Hz),
3
3
Bis(1-benzyl-1H-1,2,3-triazol-4-yl) (2,2,2-trifluoro-
4.15 q (2H, MeCH2O, JHH = 7.1, JHP = 7.1 Hz), 4.64
1
d. d (4H, ≡CCH2O, JHP = 10.2, JHH = 2.4 Hz). 13С
3
4
ethyl) phosphate (4a). Н NMR spectrum (CDCl3), δ,
ppm: 4.05 d. q (2H, CF3CH2, 3JHP = 6.3, 3JHF = 8.9 Hz),
4.91 d (4H, triazole-CH2O, 3JHP = 8.1 Hz), 5.38 s (4Н,
PhCH2), 7.14‒7.27 m (10Н, Ph), 7.55 s (2H, Htriazole).
13С NMR spectrum (CDCl3), δС, ppm: 53.9 (PhCH2),
3
NMR spectrum (CDCl3), δС, ppm: 15.5 d (Me, JCP
6.9 Hz), 54.7 d (≡CCH2O, JCP = 4.3 Hz), 64.2 d
=
2
2
(MeCH2O, JCP = 6.0 Hz), 75.7 (CH≡), 76.9 d (C≡,
3JCP = 7.7 Hz). 31P NMR spectrum (CDCl3): δP
–0.3 ppm. Found, %: С 47.82; H 5.47; P 15.13.
C8H11O4P. Calculated, %: C 47.53; H 5.48; P 15.32.
2
59.1 d (triazole-CH2O, JCP = 5.4 Hz), 62.5 q. d
2
2
(CF3CH2, JCF = 35.5, JCP = 4.3 Hz), 123.9 q. d (CF3,
3
1JCF = 278.0, JCP = 10.9 Hz), 123.0 (С5triazole), 128.0
Bis(2-propynyl) propyl phosphate (3d). Yield
3.6 g (42%), colorless liquid, bp 87‒89°C (0.4 mmHg),
d420 1.1206, nD20 1.4511 (nD20 1.4512 [21]). IR spectrum,
ν, cm–1: 3295 s, 3228 s, 2972 s, 2942 m, 2901 m, 2882
m, 2743 w, 2689 w, 2438 w, 2128 s, 1922 w, 1817 w,
1623 w, 1455 m, 1394 m, 1375 m, 1351 m, 1277 s,
1153 m, 1029 s, 994 s, 944 s, 910 m, 873 m, 782 m,
(Сo), 128.5 (Сp), 128.9 (Сm), 134.6 (Cipso), 146.0 d
(С4triazole, JCP = 7.9 Hz). N NMR spectrum (CDCl3),
δN, ppm:–132.0 (N1), –32.0 (N3), –20.0 (N2). 19F NMR
spectrum (CDCl3), δF, ppm: –74.9 t (CF3, 3JHF = 8.8 Hz).
31P NMR spectrum (CDCl3): δP –1.0 ppm. Mass
spectrum, m/z (Irel, %): 522 (0.2) [M]+.
3
15
1
688 m, 648 m, 558 m, 383 m. Н NMR spectrum
Bis(1-benzyl-1H-1,2,3-triazol-4-yl) (2,2,3,3-tetra-
3
(CDCl3), δ, ppm: 0.95 t (3H, Me, JHH = 7.5 Hz), 1.71
1
fluoropropyl) phosphate (4b). Н NMR spectrum
3
sextet (2H, MeCH2, JHH = 7.1 Hz), 2.56 t (2H, CH≡,
(CDCl3), δ, ppm: 4.07 t. d (2H, CF2CH2O, 3JHF = 12.7,
3JHP = 5.7 Hz), 4.94 d (triazole-CH2O, 3JHP2 = 7.0 Hz),
5.41 s (4Н, PhCH2), 5.94 t. t (1H, CHF2, JHF = 52.0,
3JHF = 5.8 Hz), 7.17‒7.45 m (10Н, Ph), 7.57 s (2H,
3
4JHH = 2.3 Hz), 4.05 d. q (2H, EtCH2O, JHH = 6.9,
3
3JHP = 6.9 Hz), 4.67 d. d (4H, ≡CCH2O, JHP = 10.1,
4JHH = 2.3 Hz). 13С NMR spectrum (CDCl3), δС, ppm:
3
10.0 (Me), 23.6 d (MeCH2, JCP = 7.2 Hz), 55.2 d
H
triazole). 13С NMR spectrum (DMSO-d6), δС, ppm:
2
2
(≡CCH2O, JCP = 4.9 Hz), 70.1 d (EtCH2O, JCP
=
2
53.0 (PhCH2), 59.1 d (triazole-CH2O, JCP = 5.0 Hz),
6.1 Hz), 76.1 (CH≡), 77.5 d (C≡, JCP = 7.8 Hz). 31P
NMR spectrum (CDCl3): δP –0.2 ppm. Found, %: C
50.05; H 6.12; P 14.05. C9H13O4P. Calculated, %: C
50.01; H 6.06; P 14.33.
3
1
62.4 m (CF2CH2O), 110.3 t. t (CHF2, JCF = 247.5,
2JCF = 32.3 Hz), 116.4 t. t. d (CF2, 1JCF = 248.9, 2JCF
=
25.4, 3JCP = 9.3 Hz), 124.9 (С5triazole), 128.9 (Сo), 129.7
(Сm), 131.1 (Сp), 137.1 (Cipso), 146.2 d (С4triazole, JCP
=
3
8.5 Hz). 15N NMR spectrum (DMSO-d6), δN, ppm:
–130.1 (N1), –28.3 (N3), –18.5 (N2). 19F NMR
spectrum (DMSO-d6), δF, ppm: –139.7 d. t (CHF2,
General procedure for the synthesis of bis(1-
benzyl-1H-1,2,3-triazol-4-yl) alkyl phosphates (4a,
4b, 4d). To a solution of bis(2-propynyl) alkyl
phosphate 3 (0.85 mmol) in 2 mL of acetonitrile were
successively added benzyl chloride (1.7 mmol,
0.215 g), sodium azide (1.7 mmol, 0.11 g),
CuSO4·5H2O (0.05 mmol, 0.01 g), sodium ascorbate
(0.18 mmol) and triethylamine (1.7 mmol, 0.172 g).
Sodium ascorbate was used in the form of a freshly
prepared aqueous solution, which was obtained from
ascorbic acid (0.18 mmol, 0.32 g), NaOH (0.18 mmol,
0.07 g), and 0.2 mL of H2O. The reaction mixture was
stirred under nitrogen at room temperature for 4 (3a,
3b) or 7 h (3d), then filtered. The solvent was distilled
off under reduced pressure, and the residue was dried
in vacuum and analyzed. According to NMR
spectroscopy (1H, 13C, 15N, 19F, 31P), the resulting
product was a mixture of bis(1-benzyl-1H-1,2,3-triazol-
4-yl) alkyl phosphate 4, triethylammonium hydro-
chloride and triethylbenzylammonium chloride (were
2JHF = 52.2, JFF = 6.6 Hz), –126.0 m (CF2). P NMR
3
31
spectrum (CDCl3): δP –0.9 ppm.
Bis(1-benzyl-1H-1,2,3-triazol-4-yl) propyl phos-
phate (4d). 1Н NMR spectrum (CDCl3), δ, ppm: 0.81 t
3
(3H, Me, JHH = 7.4 Hz), 1.51 sextet (2H, MeCH2,
3JHH = 7.4 Hz), 3.72 d. t (2H, EtCH2O, 3JHH = 7.4, 3JHP
=
7.0 Hz), 4.97 d (triazole-CH2O, 3JHP = 6.9 Hz), 5.43 s
(4Н, PhCH2), 7.20‒7.48 m (10Н, Ph), 7.62 s (2H,
H
triazole). 13С NMR spectrum (DMSO-d6), δС, ppm:
3
11.3 (Me), 24.5 d (MeCH2, JCP = 7.3 Hz), 53.7
(PhCH2), 59.0 d (triazole-CH2O, 2JCP = 4.8 Hz), 66.9 d
(EtCH2O, JCP = 5.8 Hz), 124.9 (С5triazole), 128.9 (Сo),
2
129.7 (Сm), 133.6 (Сp), 137.1 (Cipso), 146.2 d (С4
,
triazole
3JCP = 8.4 Hz). 15N NMR spectrum (DMSO-d6), δN,
ppm: –130.1 (N1), –27.8 (N3), –18.6 (N2). 31P NMR
spectrum (CDCl3): δP 0.2 ppm.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 4 2019

712
VERKHOTUROVA et al.
no. 11, p. 1623. doi 10.1134/S107042801711001X
FUNDING
11. Gusarova, N.K., Verkhoturova, S.I., Arbuzova, S.N.,
Kazantseva, T.I., Albanov, A.I., Nalibaeva, A.M.,
Bishimbaeva, G.K., Apartsin, K.A., Kireeva, V.V., and
Trofimov, B.A., Russ. J. Gen. Chem., 2018, vol. 88,
no. 4, p. 705. doi 10.1134/S107036321804014Х
The work was performed using equipment of the
Baikal Analytical Center for Collective Use of the
Siberian Branch of the Russian Academy of Sciences.
CONFLICT OF INTEREST
No conflict of interest was declared by the authors.
REFERENCES
12. Trofimov, B.A. and Gusarova, N.K., Russ. Chem. Rev.,
2007, vol. 76, no. 6, p. 550. doi 10.1070/
RC2007v076n06ABEH003712
13. Gusarova, N.K., Chernysheva, N.A., and Trofimov, B.A.,
Synthesis, 2017, vol. 49, no. 21, p. 4783. doi 10.1055/s-
0036-1588542
1. Zhang, S.S., J. Power Sources, 2006, vol. 162, no. 2,
p. 1379. doi 10.1016/j.jpowsour.2006.07.074
2. Han, S.-I., Shin, W.-C., Yu, J.-Y., Bae, T.-H., Lee, M.-H.,
Chernyshov, D., Tereshchenko, A., Shatunov, P., Trofi-
mov, B.A., and Gusarova, N.K., USA Patent
20120244445, 2012; C. A., 2012, vol. 157, p. 525496.
14. Voronin, V.V., Ledovskaya, M.S., Bogachenkov, A.S.,
Rodygin, K.S., and Ananikov, V.P., Molecules, 2018,
vol. 23, no. 10, p. 2442. doi 10.3390/
molecules23102442
3. Takase, H. and Yokotsuji, H., EU Patent 3038194 A1
15. Rostovtsev, V.V., Green, L.G., Fokin, V.V., and
Sharpless, K.B., Angew. Chem. Int. Ed., 2002, vol. 41,
no. 14, p. 2596. doi 10.1002/1521-3773(20020715)41
20160629, 2016; C. A., 2016, vol. 165, p. 155467.
4. Aspern, N., Röser, S., Rad, B.R., Murmann, P., Streipert, B.,
Mönnighoff, X., Tillmann, S.D., Shevchuk, M.,
Stubbmann-Kazakova, O., Röschenthaler, G.-V., Nowak, S.,
Winter, M., and Cekic-Laskovic, I., J. Fluor. Chem.,
16. Grischenko, L.A., Parshina, L.N., Larina, L.I.,
Novikova, L.N., and Trofimov, B.A., Carbohydrate
Polymers, 2015, vol. 115, p. 294. doi 10.1016/
j.carbpol.2014.08.050
2017,
vol.
198,
p.
24.
doi
10.1016/
j.jfluchem.2017.02.005
17. Erzunov, D.A., Latyshev, G.V., Averin, A.D.,
Beletskaya, I.P., and Lukashev, N.V., Eur. J. Org.
Chem., 2015, vol. 2015, no. 28, p. 6289. doi 10.1002/
ejoc.201500835
5. Su, C.-C., He, M., Peebles, C., Zeng, L., Tornheim, A.,
Liao, C., Zhang, L., Wang, J., Wang, Y., and Zhang, Z.,
ACS Appl. Mater. Interfaces, 2017, vol. 9, no. 36,
p. 30686. doi 10.1021/acsami.7b08953
18. Starodubtseva, R.R., Gibadullina, E.M., Pazilova, N.B.,
Syakaev, V.V., Pudovik, M.A., and Burilov, A.R., Russ.
J. Gen. Chem., 2017, vol. 87, no. 9, p. 1908. doi
10.1134/S1070363217090031
6. Peng, S., Yake, A.M., and Meng, X., USA Patent
20130210976, 2013; C. A., 2013, vol. 159, p. 349704.
7. Larichev, R.B., Meng, X., and Yake, A.M., USA Patent
8859799, 2014; C. A., 2014, vol. 161, p. 588221.
19. Gusarova, N.K., Verkhoturova, S.I., Arbuzova, S.N.,
Kazantseva, T.I., Nalibaeva, A.M., and Bishimbaeva, G.K.,
Butlerov. Commun., 2016, vol. 47, no. 8, p. 29.
8. Krutikova, V.V., Krutikov, V.I., and Erkin, A.V., Russ.
J. Gen. Chem., 2010, vol. 80, no. 3, p. 434. doi 10.1134/
S1070363210030102
20. Kormachev, V.V. and Fedoseev, M.S., Preparativnaya
khimiya fosfora (Preparative Phosphorus Chemistry),
Perm: Ural. Otd. Ross. Akad. Nauk, 1992.
9. Baszczyňski, O. and Janeba, Z., Med. Res. Rev., 2013,
vol. 33, no. 6, p. 1304. doi 10.1002/med.21296
10. Gusarova, N.K., Verkhoturova, S.I., Arbuzova, S.N.,
Kazantseva, T.I., Albanov, А.I., Nalibaeva, А.М., and
Bishimbaeva, G.K., Russ. J. Org. Chem., 2017, vol. 53,
21. Arend, G., Behrenz, W., and Block, H.-D., Germany
Patent 2727479, 1979; C. A., 1979, vol. 90, p. 138331.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 4 2019