Transesterification of dialkyl carbonates with fluorine-containing alcohols

Article abstract of DOI:10.1007/s11172-021-3169-4

Reactions of transesterification of dimethyl, diethyl and dibutyl carbonates with 2,2,3,3-tetrafluoroethyl-, 2,2,3,3,4,4,5,5-octafluorobutyl- and 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorohexyl-carbinols were investigated in the presence of various catalysts. It was found that the conversion of starting dialkyl carbonate increases upon increasing the length of fluorine-containing radical in the presence of sodium alkoxide. It was shown that the maximum conversion of dimethyl carbonate (90%) was achieved in its reaction with 2,2,3,3,4,4,5,5-octafluoropentan-1-ol upon using catalysts such as K₂CO₃, NaOH, and sodium alkoxide. To achieve similar values of the conversion, Ti(OEt)₄ and Ti(OiPr)₄ should be used in the cases of diethyl and dibutyl carbonates, respectively.

Full text of DOI:10.1007/s11172-021-3169-4

Russian Chemical Bulletin, International Edition, Vol. 70, No. 5, pp. 933—936, May, 2021
933
Transesterification of dialkyl carbonates with fluorine-containing alcohols*
А. М. Semenova,a М. G. Pervova, М. А. Ezhikova, М. I. Kodess, А. Ya. Zapevalov, and А. V. Pestov
a
a
a,b
a
a,b
aI. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences,
2
2/20 ul. Sof´i Kovalevskoy, 620108 Ekaterinburg, Russian Federation.
Е-mail: sam@ios.uran.ru
b
Ural Federal University named after the First President of Russia, B. N. Yeltsin,
9 ul. Mira, 620002 Ekaterinburg, Russian Federation
1
Reactions of transesterification of dimethyl, diethyl and dibutyl carbonates with 2,2,3,3-tetra-
fluoroethyl-, 2,2,3,3,4,4,5,5-octafluorobutyl- and 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorohexyl-
carbinols were investigated in the presence of various catalysts. It was found that the conversion
of starting dialkyl carbonate increases upon increasing the length of fluorine-containing radical
in the presence of sodium alkoxide. It was shown that the maximum conversion of dimethyl
carbonate (90%) was achieved in its reaction with 2,2,3,3,4,4,5,5-octafluoropentan-1-ol upon
using catalysts such as K CO , NaOH, and sodium alkoxide. To achieve similar values of the
2
3
conversion, Ti(OEt) and Ti(OiPr) should be used in the cases of diethyl and dibutyl carbon-
4
4
ates, respectively.
Key words: transesterification, polyfluorinated alcohols, telomer alcohols, dialkyl carbonates.
An introduction of fluorine atoms or fluorinated func-
tional groups into hydrocarbon-containing compounds
allows obtaining derivatives possessing unique physical,
biological, and chemical properties.1 Fluor-containing
esters of carbonic acid, viz. fluorinated dialkyl carbonates,
are underexplored compounds, but have recently attracted
significant interest due to the opportunity to use them as
solvents both in chemical sources of electrical energy and
for carrying out specific chemical reactions. The presence
of fluorine atoms in organic carbonates maintains a high
action media causing a negative effect on the environment
were used in all those cases. A method for the preparation
of dialkyl carbonates using diphenyl carbonate in the pres-
ence of amines allows obtaining only non-fluorinated
—5
1
7
dialkyl carbonates.
The present work was aimed at the one-step trans-
esterification reaction of dimethyl (1a), diethyl (1b),
and dibutyl (1c) carbonates with 2,2,3,3-tetrafluoro-
ethyl- (2a), 2,2,3,3,4,4,5,5-octafluorobutyl- (2b), and
2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorohexylcarbinol (2c) in
the presence of various catalysts in order to develop
methods for the preparation of fluorine-containing dialkyl
carbonates.
6
dielectric constant and low viscosity, which improves the
solubility of alkali metal salts upon preparation of an
electrolyte, as compared to hydrocarbon analogs, and also
leads to a wide temperature range of their practical
7
—10
use.
Polyfluorinated carbonates are also employed as
Results and Discussion
valuable highly reactive intermediates for the preparation
1
1,12
of various derivatives, e.g., carbamates
and non-
symmetric aliphatic ureas.13
To develop methods for the production of organic
carbonates based on 2,2,3,3-tetrafluoropropan-1-ol (2a)
as modern "green" reagents and solvents,1 the trans-
The traditional method for the synthesis of dialkyl
8
carbonates, including fluorine-containing ones, is a reac-
1
9
tion of alcohols with phosgene.14 Another method based
esterification reaction of dimethyl carbonate and titan-
2
0
ium(IV) tetraalkoxides has been investigated in details.
It was impossible under those conditions to obtain carbon-
ates containing more than four carbon atoms in a fluorine-
containing hydrocarbon radical. A subsequent two-step
transesterification of titanium(IV) alkoxides based on
polyfluoroalkan-1-ol allowed obtaining a mixture of alkyl-
polyfluoroalkyl carbonate and bispolyfluoroalkyl carbon-
ate in the yields of 50—80%. Taking into account the
opportunity to efficiently utilize 2,2,3,3-tetrafluoropropan-
1-ol (n = 1) (2a), 2,2,3,3,4,4,5,5-octafluoropentan-1-ol
on the reaction of 2,2,3,3-tetrafluoropropan-1-ol with
CCl in the presence of AlCl was reported for the prepa-
4
3
1
5
ration of polyfluorinated carbonates. The synthesis of
polyfluorinated carbonates in methanol is covered by
1
6
a patent, whereas there are no any analytical nor spectral
data characterizing the composition and structure of the
products obtained. Toxic, explosive, and aggressive re-
*
Dedicated to Academician of the Russian Academy of Sciences
V. N. Charushin on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 933—936, May, 2021.
066-5285/21/7005-0933 © 2021 Springer Science+Business Media LLC
1

9
34
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
Semenova et al.
Scheme 1
1
3
: R = Me (a), Et (b), Bu (c); 2, 4: n = 1 (a), 2 (b), 3 (c);
: R = Me, n = 1 (a), 2 (b), 3 (c); R = Et, n = 1 (d), 2 (e), 3 (f); R = Bu, n = 1 (g), 2 (h), 3 (i)
(
n = 2) (2b), and 2,2,3,3,4,4,5,5,6,6,6,7,7-dodecafluoro-
ensure a high conversion of alcohol into the carbonate,
while sodium compounds exhibited an increased activity
compared to potassium compounds. It should be noted
heptan-1-ol (n = 3) (2c) in the synthesis of fluorine-
containing dialkyl carbonates via a one-step transesterific-
ation, we performed herein a competitive comparison of
the catalytic activity of various Lewis acids and bases, de-
pending on the structure of the starting reagents (Scheme 1).
Obtained products 3a—i and 4a—c were separated
using a fractional distillation, and the ratio between the
reaction products was estimated using gas-liquid chroma-
that Na CO exhibited the lowest activity not only in the
2
3
comparison with K CO , but also among all the studied
2
3
catalysts. Titanium(IV) ethoxide is an efficient Lewis acid,
2
1,22
including the transesterification reaction,
but did not
show any activity in our case. However, in the case of
transesterification of diethyl (1b) and dibutyl (1c) carbon-
ates with fluorine-substituted carbinols, titanium(IV)
alkoxide exhibited a catalytic activity. Thus, the con-
version of diethyl carbonate (1b) in its reaction with
2,2,3,3,4,4,5,5-octafluoropentan-1-ol (2b) in the presence
of tetraethoxytitanium reached 89%, while that in the case
of dibutyl carbonate was 63%. Using titanium tetraiso-
propoxide allowed us to increase the conversion up to 88%.
1
tography (GLC) and H NMR spectroscopy. According
to the acquired data (Table 1), the reaction of dialkyl
carbonates 1a—c with 2,2,3,3,4,4,5,5-octafluoropentan-
1
-ol (2b) proceeds to give a mixture of alkyl-2,2,3,3,4,4,5,5-
octafluoropentyl carbonate (3b,e,h) and bis(2,2,3,3,4,4,5,5-
octafluoropentyl) carbonate (4b) (see Scheme 1). In the
case of dimethyl carbonate 1a, hydroxides and alkoxides
Table 1. Transesterification of dialkyl carbonates (1a—c) with 2,2,3,3,4,4,5,5-octafluoropentan-1-ol (2b) in the
presence of various catalysts
Catalyst
Carbonate
Molar ratio
b : carbonate
Conversion
of 2 (%)
Products
Ratio of
products
2
NaOH
1a
1a
1a
1a
1a
1a
1a
1a
1b
1b
1b
1b
1b
1c
1c
1c
1c
1c
1c
1c
1c
1c
1c
1c
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.85
1 : 0.68
1 : 0.5
1 : 0.5
1 : 0.85
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
1 : 0.5
89
71
85
90
71
43
89
0
79
89
53
83
86
70
50
47
63
88
43
70
47
47
65
50
3b + 4b
3b + 4b
3b + 4b
3b + 4b
3b + 4b
3b + 4b
3b + 4b
3b + 4b
3e + 4b
3e + 4b
3e + 4b
3e + 4b
3e + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
3h + 4b
1 : 32
1 : 2.3
1 : 7.1
1 : 2
KOH
+
–
Me N OH
4
NaOR
KOR
1 : 2
Na CO3
K CO3
1 : 2
1 : 26
—
2.8 : 1
1 : 1
1 : 0.14
2 : 1
1 : 1.4
2.3 : 0
1 : 0
0.9 : 0
1.7 : 0
1 : 2
0.8 : 0
2.3 : 0
0.9 : 0
0.9 : 0
12 : 1
1 : 0
2
2
Ti(OEt)4
NaOR
Ti(OEt)4
Ti(OEt)4
NaOR
Ti(OEt)4
Ti(OBu)4
NaOR
Imidazole
Ti(OEt)4
i
Ti(OPr )4
Ti(OBu)4
Al(secBuO)
3
t
Sn(Bu O)3
BF •Et O
3
2
SnCl •1,4-dioxane
2
SnCl •THF
4

Fluor-containing dialkyl carbonates
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
935
Table 2. Transesterification of dialkyl carbonates (1a—c) with
fluorine-containing alcohols (2a—c) in the presence of sodium
alkoxide*
relative to the solvent residual signal (δ = 39.5). IR spectra were
C
recorded on a Nicolet 6700 spectrometer equipped with an ATR
module with a diamond crystal for the range of 400—4000 cm–1
.
Elemental analysis was performed on a Perkin Elmer CHN PE
400 automatic analyzer. Chromatographic analysis was carried
2
Alcohol 2 Carbonate Conversion Products
of 2 (%)
Ratio of
products
out using a Shimadzu GC2010 gas—liquid chromatograph
equipped with a flame ionization detector and a ZB-5 quartz
capillary column (length of 30 m, diameter of 0.25 mm, film
2
2
2
2
2
2
2
2
2
a
a
a
b
b
b
c
c
c
1a
1b
1c
1a
1b
1c
1a
1b
1c
25
18
16
90
79
79
65
66
78
3a + 4a
3d + 4a
3g + 4c
3b + 4b
3e + 4b
3h + 4b
3c + 4c
3f + 4c
3i + 4c
2.1 : 1
9.3 : 1
1 : 0
thickness of 0.25 μm); nebulizer gas N , split flow 1 : 30. The
2
initial column temperature was 40 °C (isotherm 3 min), the
temperature was then increased at the rate of 10 °C min–1 up to
280 °C (isotherm 15 min), and temperatures of the evaporator
and detector were 250 and 300 °С, respectively.
Transesterification (general procedure). A catalyst (1.5 mmol)
was added to a mixture of hydropolyfluoroalkan-1-ol (0.1 mol)
and dialkyl carbonate (0.085 mol), and the mixture was heated
up to reflux. The reaction mass was fractionally distilled at the
temperatures >110 °С in the case of 2,2,3,3-tetrafluoropropan-
1 : 2
2.8 : 1
2 : 1
1 : 3.2
1 : 2
2.9 : 1
*
The molar ratio of starting reagents was alcohol 2a—c : dialkyl
carbonate 1a—c = 1 : 0.85.
1
1
-ol, >140 °С in the case of 2,2,3,3,4,4,5,5-octafluoropentan-
-ol (98%), and >170 °С for 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-
Overall reactivity of the starting carbonates decreases23
heptan-1-ol. The composition of obtained products was analyzed
1
using GLC and H NMR spectroscopy.
in the series of 1a, 1b, and 1c, which results in a change
in the selectivity of formation of fluorine-substituted carb-
onates 3a—i and 4a—c regardless of the alcohol used. The
comparison of reactivity of fluorinated alcohols under the
conditions of considered transesterification reaction re-
vealed that in the case of carbonates 1a and 1b, the
maximum reactivity was achived for 2,2,3,3,4,4,5,5-octa-
fluoropentan-1-ol (2b) (Table 2). In the case of dibutyl
carbonate 1c, the reactivity of polyfluorinated alcohols 2b
and 2c was the same.
In summary, the present work revealed that fluorine-
containing alcohols can efficiently undergo the trans-
esterification reaction in the presence of Lewis both acids
and bases. The conversion of dialkyl carbonates increases
with the length of fluorine-containing radical and de-
pends on the composition of carbonate. The maximum
conversion of dimethyl carbonate 1a in the reaction with
Sodium and potassium alkoxides were generated in situ by
adding certain amounts of metallic sodium or potassium tert-
butoxide, respectively.
Ethyl(2,2,3,3-tetrafluoropropyl)carbonate 3d. The yield was
2
0
7.96 g (13%). Colorless liquid, b.p. 155—156 °С, n
1.340. IR,
D
–
1
ν/cm : 2990 (С—Н), 1762 (С=О), 1271 (С—F), 1108 (С—О).
1
H NMR (DMSO-d ), δ: 1.24 (t, 3 Н, CH , J = 7.1 Hz); 4.20
6
3
(
q, 2 Н, ОCH СН , J = 7.1 Hz); 4.65 (t, 2 Н, ОCH СF ,
2 3 2 2
J = 14.2 Hz); 6.61 (tt, 1 H, CF H, J = 51.8 Hz, J = 5.2 Hz).
2
1
3
C NMR (DMSO-d ), δ: 13.79 (CH ); 62.38 (t, OCH CF ,
6
3
2
2
J = 26.8 Hz); 64.78 (OCH CH ); 109.23 (tt, CF H, J = 248.0 Hz,
2
3
2
J = 33.3 Hz); 114.27 (tt, OCH CF , J = 249.4 Hz, J = 26.7 Hz);
2
2
19
1
53.62 (CO). F NMR (DMSO-d ), δ: 23.89 (dt, 2 F, CF H,
6
2
J = 51.8 Hz, J = 5.2 Hz); 37.5 (tq, 2 F, ОCH СF , J = 14.2 Hz,
2
2
J = 5.2 Hz). Found (%): С, 35.10; Н, 3.95; F, 37.03. C6H8F4O3.
Calculated (%): С, 35.30; Н, 3.95; F, 37.23.
Bis(2,2,3,3-tetrafluoropropyl)carbonate 4a. The yield was
20
–1
1
2
(
7%. Colorless liquid, b.p. 181—182 °C, nD 1.335. IR, ν/cm
:
1
983 (С—Н), 1778 (С=О), 1279 (С—F), 1108 (C—O). H NMR
2
,2,3,3,4,4,5,5-octafluoropentan-1-ol 2b was achieved
DMSO-d ), δ: 4.77 (t, 4 Н, ОCH СF , J = 14.2 Hz); 6.63 (tt,
6 2 2
in the cases of using K CO , NaOH, and sodium alk-
13
2
3
2 H, CF H, J = 51.8 Hz, J = 5.2 Hz). C NMR (DMSO-d ),
2
6
oxide. Titanium(IV) alkoxides maintain a comparable
conversion of diethyl and dibutyl carbonates only in
the cases of 2,2,3,3,4,4,5,5-octafluoropentan-1-ol and
δ: 63.41 (t, OCH CF , J = 26.7 Hz); 109.22 (tt, CF H,
2
2
2
J = 248.1 Hz, J = 33.2 Hz); 114.14 (tt, OCH CF , J = 249.7 Hz,
2
2
1
9
J = 26.9 Hz); 152.97 (CO). F NMR (DMSO-d ), δ: 23.95 (dt,
6
2
,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptan-1-ol.
4 F, CF2H, J = 51.8 Hz, J = 5.2 Hz); 37.55 (tk, 4 F, ОCH2СF2,
J = 14.2 Hz, J =5.2 Hz). Found (%): С, 28.95; Н, 2.07; F, 52.21.
C H F O . Calculated (%): С, 28.98; Н, 2.08; F, 52.39.
7
6
8
3
Experimental
Ethyl(2,2,3,3,4,4,5,5-octafluoropentyl)carbonate 3e. The
2
0
yield was 15%. Colorless liquid, b.p. 193—195 °C, n
1.339.
D
–
1
2
,2,3,3-Tetrafluoropropan-1-ol (98%), 2,2,3,3,4,4,5,5-octa-
IR, ν/cm : 2991 (С—Н), 1764 (С=О), 1267 (С—F), 1127
1
fluoropentan-1-ol (98%), and 2,2,3,3,4,4,5,5,6,6,7,7-dodeca-
fluoroheptan-1-ol (98%, HaloPolymer Perm, Russia) and other
reagents (AlfaAesar) were used as received without any addi-
tional purification.
(С—О). H NMR (CDCl ), δ: 1.34 (t, 3 Н, CH , J = 7.1 Hz);
3
3
4.28 (q, 2 Н, ОCH СН , J = 7.1 Hz); 4.63 (t, 2 Н, ОCH СF ,
2
3
2
2
J = 13.6 Hz); 6.06 (tt, 1 H, CF H, J = 51.9 Hz, J = 5.4 Hz).
2
1
3
C NMR (DMSO-d ), δ: 13.85 (CH ); 62.94 (t, OCH CF ,
6
3
2
2
1H (400 MHz), 19F (376 MHz), and 13C (126 MHz) NMR
J = 26.1 Hz); 64.86 (OCH CH ); 109.24 (tt, CF H, J = 251.4 Hz,
2 3 2
spectra were recorded using Bruker AVANCE-500 and DRX-400
J = 30.9 Hz); 107.3—113.5 (m, 2 CF ); 114.21 (tt, CH CF ,
2 2 2
1
19
spectrometers for solutions in CDCl and DMSO-d . The H
J = 256.8 Hz, J = 31.2 Hz); 153.21 (CO). F NMR (CDCl ),
3
6
3
1
9
and F chemical shifts are given relative to the internal standards
SiMe and C F , respectively, while those of C are reported
δ: 24.68 (dm, 2 F, CF H, J = 51.9 Hz); 31.94 (m, 2 F, CF );
2 2
1
3
36.54 (m, 2 F, CF ); 41.72 (m, 2 F, OCH CF ). Found (%):
4
6
6
2 2 2

9
36
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 5, May, 2021
Semenova et al.
С, 31.60; H, 2.70; F, 50.03. C H F O Calculated (%): С, 31.59;
Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov,
V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin,
V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov,
E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima,
A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina,
K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A.
Usachev, Russ. Chem. Rev., 2019, 88, 425; DOI: 10.1070/
RCR4871.
7. N. Azimi, W. Weng, C. Takoudis, Z. Zhang, Electrochem.
Commun., 2013, 37, 96; DOI: 10.1016/j.elecom.2013.10.020.
8. D. Nishikawa, T. Nakajima, Y. Ohzawa, M. Koh, A. Yama-
uchi, M. Kagawa, H. Aoyama, J. Power Sources, 2013, 243,
573; DOI: 10.1016/j.jpowsour.2013.06.034.
8
8
8
3.
H, 2.65; F, 49.97.
Bis(2,2,3,3,4,4,5,5-octafluoropentyl)carbonate 4b. The yield
2
0
–1
was 18%. Colorless liquid, b.p. 234—235 °C, nD 1.324. IR, ν/cm
:
1
2
986 (С—Н), 1780 (С=О), 1274 (С—F), 1124 (С—О). H NMR
(
DMSO-d ), δ: 5.00 (t, 4 Н, ОCH , J = 14.2 Hz); 7.07 (tt, 2 H,
6
2
1
3
CF H, J = 50.2 Hz, J = 5.6 Hz). C NMR (DMSO-d ), δ: 63.07
2
6
(
t, OCH2, J = 26.2 Hz); 109.22 (tt, CF H, J = 251.4 Hz,
2
J = 30.7 Hz); 107.8—113.0 (m, 2 CF ); 114.27 (tt, CH CF ,
2
2
2
1
9
J = 257.1 Hz, J = 31.0 Hz); 152.61 (CO). F NMR (DMSO-d ),
6
δ: 24.30 (dm, 4 F, CF H, J = 50.2 Hz); 33.23 (m, 4 F, CF );
2
2
3
8.03 (m, 4 F, CF ); 43.22 (m, 4 F, OCH CF ). Found (%):
2 2 2
С, 26.71; Н, 1.14; F, 62.03. C H F O . Calculated (%): С, 26.96;
7
6
8
3
Н, 1.23; F, 62.02.
Bis(2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptyl)carbonate 4c.
9. Y. Matsuda, T. Nakajima, Y. Ohzawa, M. Koh, A. Yamauchi,
M. Kagawa, H. Aoyama, J. Fluorine Chem., 2011, 132, 1174;
DOI: 10.1016/j.jfluchem.2011.07.019.
10. Yu. Sasaki, M. Takehara, S. Watanabe, N. Nanbu, M. Ue,
J. Fluorine Chem., 2004, 125, 1205; DOI: 10.1016/j.jfluchem.
2004.05.008.
11. Yu. N. Studnev, V. A. Frolovskii, O. F. Kinash, V. P. Stolyarov,
Pharm. Chem. J., 2006, 40, 76; DOI: 10.1007/s11094-006-
0062-2F.
12. T. I. Gorbunova, A. V. Pestov, A. Ya. Zapevalov, Russ. J. Appl.
Chem., 2018, 91, 657; DOI: 10.1134/S1070427218040195.
13. A. V. Bogolubsky, Yu. S. Moroz, P. K. Mykhailiuk, D. S.
Granat, S. E. Pipko, A. I. Konovets, R. Doroschuk, A. Tol-
machev, ACS Combin. Sci., 2014, 16, 303; DOI: 10.1021/
co500025f.
20
The yield was 21%. Colorless liquid, b.p. 300—301 °C, n
1.325.
D
–
1
IR, ν/cm : 2987 (С—Н), 1781 (С=О), 1279 (C—F), 1140
1
(
C—O). H NMR (DMSO-d ), δ: 5.03 (t, 4 Н, ОCH , J = 13.8 Hz),
6
2
1
3
7
.14 (tt, 2 H, CF H, J = 50.2 Hz, J = 5.3 Hz). C NMR
2
(
DMSO-d ), δ: 63.06 (t, OCH J = 26.8 Hz); 107.88 (tt, CF H,
6
2,
2
J = 252.0 Hz, J = 31.1 Hz); 108.0—116.6 (m, 5 CF ); 152.50
2
(
3
4
CO). 19F NMR (DMSO-d ), δ: 24.23 (dm, 4 F, CF H, J= 50.2 Hz);
6
2
3.64 (m, 4 F, CF ); 39.57 (m, 8 F, CF ); 40.55 (m, 4 F, CF );
2
2
2
3.49 (q, 4 F, OCH CF , J = 13.8 Hz). Found (%): С, 26.11;
2
2
Н, 0.80; F, 65.98. C H F O . Calculated (%): С, 26.10; Н, 0.88;
1
5
6 24 3
F, 66.06.
This work was carried out within the framework of the
State Assignment to the I. Ya. Postovsky Institute of
Organic Synthesis of the Ural Branch of the Russian Academy
of Sciences (Topic Nos AAAA-A19-119012290116-9 and
AAAA-A19-119012490006-1) using the equipment of the
Center for Joint Use "Spectroscopy and Analysis of
Organic Compounds".
14. H. Babad, A. Zeiler, Chem. Rev., 1973, 73, 75; DOI: 10.1021/
cr60281a005.
1
5. T. D. Petrova, A. G. Ryabichev, T. I. Savchenko, I. V. Koles-
nikova, V. E. Platonov, Zhurn. organ. khimii [J. Org. Chem.],
988, 24, 1513 (in Russian).
6. CN Pat. 109574837; Сhem. Аbstrs., 2019, 171, 294904.
7. T. Banno, K. Kawada, Sh. Matsumura, J. Surfact. Deterg.,
010, 13, 387; DOI: 10.1007/s11743-010-1224-5.
8. F. Arico, P. Tundo, Russ. Chem. Rev., 2010, 79, 479; DOI:
1
1
1
This paper does not contain descriptions of studies on
animals or humans.
2
1
The authors declare no competing interests.
10.1070/RC2010v079n06ABEH004113.
1
9. А. М. Semenova, М. G. Pervova, М. А. Ezhikova, М. I.
Kodess, А. Ya. Zapevalov, А. V. Pestov, Russ. J. Org. Chem.,
References
2
019, 55, 771; DOI: 10.1134/S0514749219060053.
2
2
2
2
0. А. М. Semenova, М. А. Ezhikova, М. I. Kodess, А. Ya.
Zapevalov, А. V. Pestov, Russ. J. Org. Chem., 2020, 56, 645;
DOI: 10.31857/S0514749220040126.
1. Y. G. Yatluk, A. L. Suvorov, E. A. Khrustaleva, S. V.
Chernyak, Russ. J. Org. Chem., 2004, 40, 769; DOI: 10.1023/
B:RUJO.0000044537.64421.dd.
2. V. A. Kuznetsov, A. V. Pestov, M. G. Pervova, Y. G. Yatluk,
Russ. J. Оrg. Сhem., 2013, 49, 1078; DOI: 10.1134/
S1070428013070208.
3. A. M. Semenova, E. F. Zhilina, A. V. Mekhaev, A. Ya.
Zapevalov, A. V. Pestov, Russ. Chem. Bull., 2020, 69, 265;
DOI: 10.1007/s11172-020-2755-1.
1
. V. Prakash Reddy, Organofluorine Chemistry: Synthesis and
Applications, Elsevier, Amsterdam, 2020.
2
3
4
5
6
. A. Yu. Rulev, A. R. Romanov, RSC Advances, 2016, 6, 1984;
DOI: 10.1039/c5ra23759a.
. V. I. Supranovich, A. D. Dilman, Mendeleev Commun., 2019,
2
9, 515; DOI: 10.1016/j.mencom.2019.09.012.
. G. A. Selivanova, E. V. Tretyakov, Russ. Chem. Bull., 2020,
9, 838.
6
. N. V. Volchkov, M. B. Lipkind, O. M. Nefedov, Russ. Chem.
Bull., 2020, 69, 68.
. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V.
Tretyakov, V. E. Platonov, P. V. Nikul´shin, A. S. Vinogradov,
Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev,
A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V.
Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov,
A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V.
Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M.
Received February 20, 2021;
in revised form March 29, 2021;
accepted March 30, 2021