Reactions of perfluoro(2,3-epoxy-2-methylpentane) with o-phenylenediamine and ethylenediamine

Article abstract of DOI:10.1134/S1070428013030068

Perfluoro(2,3-epoxy-2-methylpentane) reacted with o-phenylenediamine and ethylenediamine via cleavage of the C-C bond to produce 2,2,3,3,3-pentafluoro-N- [2-(2,2,2-trifluoro-1-trifluoromethylethylamino)-phenyl]propanamide and 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)ethyl] -propanamide, respectively. Presumably, these compounds are formed as a result of rearrangement of intermediate ketone generated by intramolecular haloform-type reaction. According to the NMR and X-ray diffraction data, 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)phenyl] propanamide in crystal exists as Z conformer with respect to the amide C-N bond.

Full text of DOI:10.1134/S1070428013030068

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2013, Vol. 49, No. 3, pp. 350–355. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © T.I. Filyakova, A.Ya. Zapevalov, M.I. Kodess, P.A. Slepukhin, V.I. Saloutin, 2013, published in Zhurnal Organicheskoi Khimii, 2013,
Vol. 49, No. 3, pp. 363–368.
Dedicated to Full Member of the Russian Academy of Sciences
I.P. Beletskaya on her jubilee
Reactions of Perfluoro(2,3-epoxy-2-methylpentane)
with o-Phenylenediamine and Ethylenediamine
T. I. Filyakova, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin, and V. I. Saloutin
Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences,
ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990 Russia
e-mail: fc403@ios.uran.ru
Received December 24, 2012
Abstract—Perfluoro(2,3-epoxy-2-methylpentane) reacted with o-phenylenediamine and ethylenediamine via
cleavage of the C–C bond to produce 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)-
phenyl]propanamide and 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)ethyl]-
propanamide, respectively. Presumably, these compounds are formed as a result of rearrangement of inter-
mediate ketone generated by intramolecular haloform-type reaction. According to the NMR and X-ray diffrac-
tion data, 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)phenyl]propanamide in
crystal exists as Z conformer with respect to the amide C–N bond.
DOI: 10.1134/S1070428013030068
Perfluorinated olefin oxides are versatile synthons
possessing a broad synthetic potential. They are ca-
pable of reacting with mono- and difunctional nucleo-
philes and electrophiles to afford various polyfunc-
tional fluorine-containing compounds and heterocyclic
systems which attract interest due to broad spectrum of
their biological and other practically useful properties
[1–11]. Reactions of mono- and disubstituted per-
fluorooxiranes with binucleophiles generally lead to
the formation of heterocyclic compounds [1–3, 7–11].
Available data on reactions of trisubstituted perfluoro-
oxiranes with binucleophiles are few in number.
We previously showed [12] that perfluoro(2,3-ep-
oxy-2-methylpentane) (hexafluoropropylene dimer
oxide, I) reacts with thiourea and urea in polar aprotic
solvents to give unusual intramolecular haloform reac-
tion products, 1-(2,2,3,3,3-pentafluoropropanoyl)-2-
(2,2,2-trifluoro-1-trifluoromethylethyl)isothiourea and
1-(2,2,3,3,3-pentafluoropropanoyl)-3-(2,2,2-trifluoro-
1-trifluoromethylethyl)urea, respectively. Hetero-
cyclization of oxirane I to 2-amino-4-pentafluoroethyl-
5,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol was
observed in its reaction with urea in weakly polar
dioxane [12].
nylenediamine and ethylenediamine in different sol-
vents with a view to elucidate how the solvent nature
affects the reaction direction and obtain new func-
tionalized fluorinated organic compounds. Unlike the
reaction with urea, oxirane I reacted with o-phenylene-
diamine (PDA) in dioxane via cleavage of the endo-
cyclic C–C bond to give 2,2,3,3,3-pentafluoro-
N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)-
phenyl]propanamide (II). A probable mechanism of
this reaction is shown in Scheme 1. Initially formed
ketone A is stabilized by intramolecular haloform-type
reaction involving attack by the amino group on the
carbonyl carbon atom; as a result, amide II is formed
instead of expected cyclization product. The ability of
poly- and perfluoroalkyl isopropyl ketones to react
with amines according to the haloform reaction pattern
was demonstrated in [13, 14].
Apart from the IR and H, 19F, and 13C NMR spec-
1
tra and elemental analysis, the structure of propan-
amide II was determined by X-ray analysis. Com-
pound II crystallized in a non-centrosymmetric space
group. Several hierarchical levels may be distinguished
in the crystal packing of II. The basic structural unit is
a skewed stack of molecules oriented along the 0a
axis. Molecules II within each stack are linked through
intermolecular hydrogen bonds NH···O formed by
In the present work we examined the reactions of
perfluoro(2,3-epoxy-2-methylpentane) (I) with o-phe-
350

REACTIONS OF PERFLUORO(2,3-EPOXY-2-METHYLPENTANE)
351
Scheme 1.
CF3
1
2
3
H
N
C6H4(NH2)2-o
dioxane, diglyme, MeCN
6'
3'
CF3
NHC(O)CF2CF3
5'
4'
1'
2'
O
–HF
1'' 2''/3''
NH'CH(CF3)2
NH
2 C2F5
F3C
F3C
C2F5
F
A
II
O
CF3
CF3
1
2
3
H
N
H2NCH2CH2NH2
dioxane, MeCN, Et2O
I
NHC(O)CF2CF3
1'
2'
O
–HF
1'' 2''/3''
NH
NH'CH(CF3)2
2 C2F5
B
III
both NH groups with the carbonyl oxygen atoms in the
neighboring molecules. This hydrogen bond is respon-
sible for the rotation of the amide fragment N2C10O1
through a dihedral angle of ~113° with respect to the
benzene ring plane and Z conformation of that frag-
ment (see figure). The CF3 groups do not participate in
specific intermolecular interactions, and they appear in
staggered conformation. The benzene rings are packed
along the [010] plane in a zigzag mode, so that the
molecules are arranged head-to-tail and the packing
becomes non-centrosymmetric. All stacks are as-
sembled into layers separated by perfluoroalkyl tails.
These layers may be regarded as the next hierarchical
level.
contained (apart from compound II as the major prod-
uct) a small amount of 2-pentafluoroethylbenzimid-
1
azole IV which was identified by H and 19F NMR;
the spectral parameters of IV coincided with those
reported in [9]. In going to more polar solvents (aceto-
nitrile, diethylene glycol dimethyl ether), the yield of
propanamide II decreased, and benzimidazole IV was
formed as the major product (in diglyme; Scheme 2).
In the reaction mixture obtained from oxirane I and
ethylenediamine we detected by IR and 19F NMR
spectroscopy a small amount of N,N′-ethylenebis-
(2,2,3,3,3-pentafluoropropanamide) (VI). Its 19F NMR
spectrum coincided with that given in [7].
Compounds IV and VI may be formed as a result
of concurrent isomerization of initial oxirane I by the
The reaction of oxirane I with ethylenediamine in
dioxane, diethyl ether, and acetonitrile led to the
formation of 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-tri-
fluoro-1-trifluoromethylethylamino)ethyl]propanamide
(III) which was isolated as a colorless viscous liquid.
Scheme 1 shows a probable mechanism of this reac-
tion. Nucleophilic opening of the oxirane ring in I via
intramolecular haloform-type reaction gives interme-
diate ketone B which undergoes rearrangement into
amide III. The structure of III was determined on the
basis of its IR, 1H, 19F, and 13C NMR, and mass spectra
and elemental composition.
F8
O1
C3
C4
F11
C11
C12
C10
C2
C5
N2
F7
F10
C6
C1
F9
N1
F5
Solvent nature was found to strongly affect the re-
action direction and yield. When the reaction of I with
PDA was carried out in dioxane, the reaction mixture
C8
F3
C7
C9
F6
F1
F4
Scheme 2.
H
NH2
N
F2
I
+
II +
C2F5
–HF
N
NH2
Molecular structure of 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-tri-
fluoro1-trifluoromethylethylamino)phenyl]propanamide (II)
according to the X-ray diffraction data.
IV
II:IV = 88:12 (dioxane), 44:56 (MeCN), 25:75 (diglyme).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 3 2013

FILYAKOVA et al.
352
Scheme 3.
NH2
NH3
NH2
+
HF
HF
+
F–
NH2
NH2
NH3
+
+
F–
NH2
H2N
H2N
O
O
H
N
F–
Nu
C2F5
H+
I
CF3
CF3
CF3
IV
C2F5
Nu
C2F5
Nu = PDA
–(CF3)2CFH
–H2O
O
CF3
F
F
C
D
Nu = EDA
–(CF3)2CFH
O
H
H
C
N
C2F5
N
C2F5
H2N
C2F5
N
H
–(CF3)2CFH
O
O
VI
action of fluoride ion; generation of the latter in the re-
action mixture is favored by increased solvent polarity.
Haloform reaction of carbanionic intermediate D in the
presence of o-phenylenediamine or ethylenediamine
leads to benzimidazole IV or bis-amide VI, respec-
tively (Scheme 3).
13C) and C6F6 as internal standards and DMSO-d6 as
solvent; the 19F chemical shifts are given relative to
CFCl3 and are positive in stronger field. Signals in the
1H and 13C NMR spectra were assigned using two-
1
dimensional heteronuclear H–13C HSQC and HMBC
techniques. The mass spectra were obtained on
a Fisons MD 800 GC–MS system (HP-5 quartz capil-
lary column, 25 m × 0.25 mm, film thickness 0.25 μm;
carrier gas helium; electron impact, 70 eV). The IR
spectra were measured in the range 400–4000 cm–1 on
a Perkin Elmer Spectrum One FT-IR spectrometer
equipped with a diffuse reflectance (DR) or attenuated
total reflectance (ATR) accessory (for solid samples).
The elemental compositions were determined on
a Perkin Elmer PE 2400 analyzer.
The yield of compounds II and III also depended
on the isolation procedure. Treatment of the reaction
mixture with water reduced the yield owing to partial
acid hydrolysis. The best yield of propanamide II was
obtained in dioxane, and of propanamide III, in diethyl
ether provided that the isolation procedure excluded
treatment with water.
Thus we have shown that the reactions of perfluori-
nated oxirane I with o-phenylenediamine and ethylene-
diamine involve cleavage of the oxirane C–C bond and
yield propanamides II and III, respectively, as a result
of regioselective nucleophilic attack on the disubstitut-
ed oxirane carbon atom and subsequent intramolecular
haloform-type reaction. The described reactions may
be regarded as a method for the preparation of new
perfluorinated propanamide derivatives which attract
interest as potential complexing agents and biologi-
cally active substances.
Oxirane I was synthesized according to the proce-
dure described in [15]. The solvents used were purified
and dried according to standard procedures.
The X-ray diffraction data for compound II were
acquired on an Xcalibur 3 automatic four-circle dif-
fractometer equipped with a CCD detector [115(2) K,
λMoKα, graphite monochromator, ω-scanning with
a step of 1°], following standard procedure. No correc-
tion for absorption was introduced, and anomalous
scattering was not evaluated. Orthohombic crystals,
space group Pna21; unit cell parameters: a = 8.3579(8),
b = 11.0885(14), c = 16.1577(16) Å; V = 1497.4(3) Å3;
Z = 4; μ = 0.209 mm–1. Total of 3399 reflection inten-
sities were measured in the range 3.05 < θ < 26.38°;
1519 reflections were independent (Rint = 0.0280);
EXPERIMENTAL
The 1H, 13C, and 19F NMR spectra were recorded on
a Bruker Avance-500 spectrometer at 500.1, 125.7, and
470.5 MHz, respectively, using tetramethylsilane (1H,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 3 2013

REACTIONS OF PERFLUORO(2,3-EPOXY-2-METHYLPENTANE)
353
completeness 95.7% for θ = 26.00°. The structure was
solved and refined using SHELX software [16]. The
refinement against F2 was performed by the full-matrix
least-squares procedure in anisotropic approximation
for all non-hydrogen atoms. Hydrogen atoms attached
to carbons were placed into positions calculated on the
basis of geometry considerations and were included in
the refinement procedure in isotropic approximation
with dependent thermal parameters according to the
riding model. The NH hydrogen atoms were localized
by the direct method, and their positions were refined
independently. The final divergence factors were R1 =
0.0265, wR2 = 0.0302 for reflections with I > 2σ(I) and
R1 = 0.0500, wR2 = 0.0313 for all reflections; goodness
of fit S = 1.011; Δρ = 0.196/–0.160 ē Å–3. The set of
crystallographic data for compound II was deposited
to the Cambridge Crystallographic Data Centre
(entry no. CCDC 924 237) and is available at
www.ccdc.cam.ac.uk/data_request/cif.
127.85 s (C6′), 128.51 s (C4′), 139.74 s (C2′), 156.27 t
2
(C1, JCF = 25.6 Hz). 19F NMR spectrum, δF, ppm:
3
71.80 d (6F, 2″-F, 3″-F, JHF = 7.0 Hz), 82.80 s (3F,
3-F), 121.99 s (2F, 2-F). Found, %: C 35.75; H 1.45;
F 51.45; N 6.97. C12H7F11N2O. Calculated, %:
C 35.64; H 1.73; F 51.73; N 6.93.
The 19F NMR spectrum of IV coincided with that
given in [9].
b. As described above in a, from 3. 65 g
(11.56 mmol) of I and 2.49 g (23 mmol) of o-phe-
nylenediamine in 30 ml of acetonitrile we obtained
4.8 g of a light brown solid which contained com-
pounds II and IV at a ratio of 44:56 (19F NMR). The
product was extracted with methylene chloride, the
extract was evaporated, and the residue, 3.02 g, was
treated as described above in a. We thus isolated 1.4 g
(30%) of compound II.
The undissolved material remaining after extraction
with methylene chloride was purified by column chro-
matography on silica gel using chloroform–methanol
(10:0.5) as eluent, followed by recrystallization from
aqueous methanol. Yield of IV 0.98 g (36%).
2,2,3,3,3-Pentafluoro-N-[2-(2,2,2-trifluoro-
1-trifluoromethylethylamino)phenyl]propanamide
(II). a. A glass ampule was charged with 1.1 g
(10.2 mmol) of o-phenylenediamine and 20 ml of
dioxane, the mixture was cooled with dry ice, 1.62 g
(5.1 mmol) of oxirane I was added, and the ampule
was sealed, allowed to warm up to room temperature,
and heated for 5 h on a water bath at ~80°C with
intermittent shaking. The ampule was then cooled and
opened, the mixture was filtered, and the filtrate was
evaporated on a Petri dish to obtain 2.4 g of a light
brown solid which contained (according to the
19F NMR data), propanamide II and benzimidazole IV
at a ratio of 88:12. The product was extracted with
methylene chloride, the extract was evaporated, and
the solid residue, 1.7 g, was purified by column chro-
matography on silica gel using methylene chloride–
hexane (3:1) as eluent, followed by recrystallization
from hexane. Yield of II 1.32 g (64%), colorless crys-
tals, mp 85–86°C. IR spectrum (DR), ν, cm–1: 3391
(NH), 3208, 2923 (C–H), 1701 (C=O), 1610 (C=Carom),
c. A glass ampule was charged with 3.3 g
(30.6 mmol) of o-phenylenediamine and 35 ml of
dioxane, the mixture was cooled with dry ice, 4.9 g
(15.5 mmol) of compound I was added, and the
ampule was sealed, allowed to warm up to room tem-
perature, and heated for 3 h on a water bath at ~80°C
with intermittent shaking. The ampule was then cooled
and opened, the mixture was poured into ice water, and
the precipitate was filtered off and dried in air at room
temperature. The product, 3.2 g, was a yellow–brown
solid which contained propanamide II and benzimid-
azole IV at a ratio of 93:7 (19F NMR). It was extracted
with methylene chloride, and the extract was evaporat-
ed. The residue, 2.6 g, was purified by column chro-
matography on silica gel using methylene chloride–
hexane (3:1) as eluent, followed by recrystallization
from hexane. Yield of II 2.1 g (35%).
1
1527 (amide II). H NMR spectrum, δ, ppm: 5.51 d
d. A glass ampule was charged with 1.8 g
(16.7 mmol) of o-phenylenediamine and 20 ml of
diglyme, the mixture was cooled with dry ice, 2.66 g
(8.4 mmol) of compound I was added, and the ampule
was sealed, allowed to warm up to room temperature,
and heated for 1 h on a water bath at ~80°C with
intermittent shaking. The ampule was then cooled and
opened, the mixture was poured into ice water, and the
precipitate was filtered off and dried in air at room
temperature. The product, 1.8 g, was a gray–brown
3
3
(1H, H′, J = 11.3 Hz), 5.92 d.sept (1H, 1″-H, J =
3
11.3, JHF = 7.0 Hz), 6.94 t.d (1H, 5′-H, J = 7.6,
1.2 Hz), 7.20 d (1H, 3′-H, J = 7.2 Hz), 7.23 d.d (1H,
6′-H, J = 7.9, J = 1.5 Hz), 7.28 d.d.d (1H, 4′-H, J = 8.2,
7.3, 1.2 Hz), 10.89 s (1H, NH). 13C NMR spectrum, δC,
2
ppm: 56.16 sept (C1″, JCF = 30.5 Hz), 106.82 t.q (C2,
1JCF = 266.4, 2JCF = 38.1 Hz), 115.43 s (C3′), 117.81 q.t
1
2
(C3, JCF = 286.8, JCF = 35.1 Hz), 120.24 s (C5′),
122.56 s (C1′), 123.75 q (C2″, C3″, JCF = 285.1 Hz),
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 3 2013

FILYAKOVA et al.
354
c. As described in b, a mixture of 5.0 g (15.8 mmol)
of oxirane I and 1.9 g (31.6 mmol) of ethylenediamine
in 30 ml of acetonitrile was heated for 4 h under reflux
with stirring. The mixture was cooled and filtered, the
filtrate was passed through a layer of silica gel to
remove tarry and salt-like impurities, the solvent was
distilled off, and the residue was subjected to fractional
distillation. Yield of III 2.9 g (52%).
solid containing propanamide II and benzimidazole IV
at a ratio of 25:75 (19F NMR). It was extracted with
methylene chloride, and the extract was evaporated.
The residue, 0.48 g, was purified by column chroma-
tography on silica gel using methylene chloride–
hexane (3:1) as eluent, followed by recrystallization
from hexane. Yield of II 0.42 g (12%). The undis-
solved material remaining after extraction with methy-
lene chloride was treated as described above in b to
isolate 0.94 g (48%) of benzimidazole IV.
d. A flask equipped with a dry-ice reflux condenser
and a magnetic stirrer was charged with 2.84 g
(47.3 mmol) of ethylenediamine and 55 ml of diethyl
ether, 7.5 g (23.7 mmol) of compound I was added,
and the mixture was stirred for 3 h at room tempera-
ture. A light yellow solid gradually separated and was
filtered off, the filtrate was passed through a layer of
silica gel to remove tarry and salt-like impurities, the
solvent was distilled off, and the residue was subjected
to fractional distillation to isolate 5.7 g (67%) of
propanamide III. According to the 19F NMR data, the
light yellow solid contained a small amount of com-
pound VI [7].
2,2,3,3,3-Pentafluoro-N-[2-(2,2,2-trifluoro-1-tri-
fluoromethylethylamino)ethyl]propanamide (III).
a. A glass ampule was charged with 2.52 g (42 mmol)
of ethylenediamine and 25 ml of dioxane, the mixture
was cooled with dry ice, 6.68 g (21 mmol) of com-
pound I was added, and the ampule was sealed,
allowed to warm up to room temperature, and heated
for 2 h on a water bath at ~80°C with intermittent
shaking. The ampule was then cooled and opened, the
mixture was poured into ice water, the organic layer
was separated and dried over MgSO4, and the product
was isolated by fractional distillation. Yield of III 3.1 g
(41%), colorless viscous liquid, bp 220–222°C. IR
spectrum (ATR), ν, cm–1: 3345 (NH); 3093, 2955,
This study was performed under financial support
by the Ural Branch of the Russian Academy of
Sciences (project no. 12-P-3-1020).
1
2885 (C–H); 1713 (C=O); 1539 (amide II). H NMR
REFERENCES
spectrum, δ, ppm: 2.94 q (2H, 2′-H, J = 6.4 Hz), 3.28–
3
3.33 m (3H, 1′-H, H′), 4.65 d.sept (1H, 1″-H, JHH
=
1. Tarrant, P., Allison, C.G., and Barthold, K.P., Fluorine
Chem. Rev., 1971, vol. 5, p. 77.
2. Millauer, H., Schwertfeger, W., and Siegemund, G.,
Angev. Chem., 1985, vol. 97, p. 164.
3. Eleuterio, H.S., J. Macromol. Sci. Part A–Chem., 1972,
3
10.5, JHF = 7.5 Hz), 9.38 br.t (1H, NH, J = 5.5 Hz).
13C NMR spectrum, δC, ppm: 39.98 (C1′), 46.34 (C2′),
2
1
59.95 sept (C1″, JCF = 29.1 Hz), 106.67 t.q (C2, JCF
=
265.2, JCF = 37.8 Hz), 117.85 q.t (C3, JCF = 286.3,
2
1
2JCF = 35.1 Hz), 123.46 q.m (C2″, C3″, 1JCF = 284.7 Hz),
vol. 6, no. 6, p. 1027.
157.04 t (C1, JCF = 25.4 Hz). 19F NMR spectrum, δF,
2
4. Ponomarenko, V.A., Krukovskii, S.P., and Alybina, A.Yu.,
Ftorsoderzhashchie geterotsepnye polimery (Fluorine-
Containing Heterochain Polymers), Moscow: Nauka,
1973, p. 50.
5. Novoe v tekhnologii soedinenii ftora (Fluorine Com-
pounds. New Technology and Application), Ishikawa, N.,
Ed., Moscow: Mir, 1984, p. 21.
6. Furin, G.G., Ftorsoderzhashchie geterotsiklicheskie soedi-
neniya. Sintez i primenenie (Fluorine-Containing Hetero-
cyclic Compounds. Synthesis and Application), Novo-
sibirsk: Nauka, 2001, p. 183.
3
ppm: 71.20 d (6F, 2″-F, 3″-F, JHF = 7.5 Hz), 84.70 s
(3F, 3-F), 125.07 s (2F, 2-F). Mass spectrum, m/z
(Irel, %): 355 (0.2) [M – H]+, 287 (5) [M – CF3]+, 193
(19), 190 (17), 180 (100), 160 (26), 124 (13), 110 (19),
69 (5.6) [CF3]+, 58 (2.6). Found, %: C 26.78; H 1.81;
F 58.96; N 7.53. C8H7F11N2O. Calculated, %: C 26.97;
H 1.97; F 58.71; N 7.87. M 356.14
b. A flask equipped with a dry-ice reflux condenser
and a magnetic stirrer was charged with 2.28 g
(38 mmol) of ethylenediamine and 35 ml of aceto-
nitrile, 6.0 g (19 mmol) of oxirane I was added
dropwise, and the mixture was heated for 4 h under
reflux with stirring, cooled, and poured into ice water.
The organic phase was separated, dried over MgSO4,
and subjected to fractional distillation. Yield of III
2.4 g (36%).
7. Saloutina, L.V., Zapevalov, A.Ya., Kodess, M.I., and
Saloutin, V.I., Russ. J. Org. Chem., 1997, vol. 33, p. 265.
8. Saloutina, L.V., Zapevalov, A.Ya., Kodess, M.I., Salo-
utin, V.I., Aleksandrov, G.G., and Chupakhin, O.N., Russ.
J. Org. Chem., 2000, vol. 36, p. 887.
9. Saloutina, L.V., Zapevalov, A.Ya., Kodess, M.I., Salo-
utin, V.I., Kirichenko, V.E., Pervova, M.G., and Chupa-
khin, O.N., Russ. J. Org. Chem., 2006, vol. 42, p. 558.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 3 2013

REACTIONS OF PERFLUORO(2,3-EPOXY-2-METHYLPENTANE)
355
13. Saloutina, L.V., Zapevalov, A.Ya., and Kolenko, I.P.,
10. Saloutina, L.V., Zapevalov, A.Ya., Saloutin, V.I.,
Kodess, M.I., and Slepukhin, P.A., Russ. J. Org. Chem.,
2009, vol. 45, p. 865.
Zh. Org. Khim., 1986, vol. 22, p. 2250.
14. Glazkov, A.A., Ignatenko, A.V., Krukovskii, S.P., and
Ponomarenko, V.A., Izv. Akad. Nauk SSSR, Ser. Khim.,
1978, p. 1570.
15. Kolenko, I.P., Filyakova, T.I., Zapevalov, A.Ya., and
Lur’e, E.P., Izv. Akad. Nauk SSSR, Ser. Khim., 1979,
no. 11, p. 2509.
11. Filyakova, T.I., Kodess, M.I., Slepukhin, P.A., and
Zapevalov, A.Ya., Russ. J. Org. Chem., 2009, vol. 45,
p. 1700.
12. Filyakova, T.I., Saloutina, L.V., Zapevalov, A.Ya.,
Slepukhin, P.A., Kodess, M.I., and Saloutin, V.I., Russ.
J. Org. Chem., 2011, vol. 47, p. 650.
16. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008,
vol. 64, p. 112.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 49 No. 3 2013