Dialkylamido sulfoxylic acid fluorides, I: Synthesis and reactions with olefins

Article abstract of DOI:10.1080/10426500902855182

The reaction of potassium fluoride with the corresponding acid chlorides results in the formation of dialkylamido sulfoxylic acid fluorides Alk2N-S-F. Stereo- and regioselectivity of dimethylamido and diisopropylamido sulfoxylic acid fluorides addition re

Full text of DOI:10.1080/10426500902855182

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Dialkylamido Sulfoxylic Acid
Fluorides, I: Synthesis and
Reactions with Olefins
Vladimir N. Kozel a , Alexander B. Rozhenko a ,
Valerij E. Pashinnik a & Yuriy G. Shermolovich a
a Institute of Organic Chemistry, National Academy
of Science of Ukraine, Kyiv, Ukraine
Version of record first published: 28 Apr 2009.
To cite this article: Vladimir N. Kozel, Alexander B. Rozhenko, Valerij E. Pashinnik
& Yuriy G. Shermolovich (2009): Dialkylamido Sulfoxylic Acid Fluorides, I: Synthesis
and Reactions with Olefins, Phosphorus, Sulfur, and Silicon and the Related Elements,
184:5, 1149-1160
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Phosphorus, Sulfur, and Silicon, 184:1149–1160, 2009
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500902855182
Dialkylamido Sulfoxylic Acid Fluorides, I: Synthesis and
Reactions with Olefins
Vladimir N. Kozel, Alexander B. Rozhenko,
Valerij E. Pashinnik, and Yuriy G. Shermolovich
Institute of Organic Chemistry, National Academy of Science
of Ukraine, Kyiv, Ukraine
The reaction of potassium fluoride with the corresponding acid chlorides results
in the formation of dialkylamido sulfoxylic acid fluorides Alk N-S-F. Stereo- and
2
regioselectivity of dimethylamido and diisopropylamido sulfoxylic acid fluorides
addition reactions to the C,C double bond in cyclohexene, 3,4-dihydro-2H-pyrane,
and vinyl ethyl ether has been investigated. This reaction is a convenient approach
to the β-fluoroalkyl sulfenic acid derivatives.
Keywords Alkenes; fluorides of dialkylamido sulfoxylic acids; fluorinating reagents;
β-fluoroalkyl sulfenic acid
INTRODUCTION
Organic compounds of four- and six-valent sulfur with sulfur-fluorine
bonds (sulfinic and sulfonic acids fluorides, SIV and SVI fluorosulfu-
ranes) are well studied and widely used in organic synthesis. An-
other situation is observed for the organic compounds of two-valent
sulfur with a sulfur fluorine bond. Arenesulfinic acid fluorides Ar-
S-F are practically unknown. Perfluoroalkyl sulfenic acid fluorides
AlkF-S-F are unstable, and their disproportion results in formation
of trifluorosulfuranes.1–4
We had shown earlier in the course of investigations on
the properties of S-organyl-S-(dialkylamino)difluorosulfuranes that
S-(benzthiazolyl-2)-S-(dialkylamino)difluorosulfurane decomposes to
Received 19 December 2007; accepted 24 February 2008.
Dedicated to Professor Marian Miko lajczyk, CBMiM PAN in Lo´dz´, Poland, on the
ꢀ
ꢀ
occasion of his 70th birthday.
Address correspondence to Yuriy G. Shermolovich, Institute of Organic Chemistry,
National Academy of Science of Ukraine, Murmanska str. 5, 02660, Kyiv, Ukraine.
E-mail: sherm@ioch.kiev.ua
1149

1150
V. N. Kozel et al.
form 2-fluorobenzthiazole and dialkylamido sulfoxylic fluorides (Alk2N-
S-F, Alk = CH3, C2H5; Alk2 = O(CH2)4, (CH2)5)5; Scheme 1).
SCHEME 1
The synthesis of hydrolytically unstable compounds of this class was
described,6–8 but their thermal stability and chemical properties have
not been studied.
The aim of the presented work is the development of a synthetic
method as well as investigation of the thermal stability and chemical
properties of dialkylamido sulfoxylic acid fluorides.
RESULTS AND DISCUSSION
We have shown that the reaction of morpholino sulfoxylic acid chloride
and potassium fluoride in acetonitrile results in the formation of the
corresponding morpholino sulfoxylic acid fluoride.5 The detailed inves-
tigation of this interaction has shown that this approach is general and
can be used to obtain also the dialkylamido sulfoxylic acid fluorides
1a,b (Scheme 2).
SCHEME 2
The reaction proceeds at room temperature for 16 h. We have not
succeeded in isolating fluorides 1a,b from the reaction mixture, as they
decompose upon solvent evaporation. However, they can be kept under
exclusion of air and moisture as acetonitrile solution for several weeks.
The peculiarity of the fluorides 1a,b is a 19F NMR resonance at high
field (–163.7 for 1a, –153.5 for 1b), which is obviously different from the
19F chemical shifts typical for derivatives of sulfuric and sulfurous acids
Alk2NSOF and Alk2NSO2F (20–70 ppm).9 It may be assumed that this
fact is evidence of a considerable contribution of the mesomeric struc-
ture B (Figure 1) to the general electronic distribution in the molecules
and, consequently, a high mobility of the fluorine atoms.

Dialkylamido Sulfoxylic Acid Fluorides
1151
FIGURE 1 Mesomeric structures of dialkylamino sulfoxylic acid fluorides.
The structure of 1a optimized at the MP2(fc)/6–311+G∗∗ level of
theory is shown in Figure 2. A detailed description of the calculation
methods is given in the Experimental section. Geometry optimiza-
tion without any symmetry restrictions leads to the Cs symmetrical
structure.
The specific feature of 1a is the practically trigonal planar configu-
ration of the nitrogen atom (sum of angles 353.6◦) and the shortened
(1.616Å) N S bond. (For comparison, the N S bond length calculated
within the same approximation for the model compound H2N-S-H is
FIGURE 2 Calculated (MP2(fc)/6–311+G∗∗) structure of 1a. Most important
structural parameters: N-S 1.616 Å; S-F 1.730 Å; NSF 105.3◦; CNS 120.1◦;
CNC 113.5◦; NSF 75.0◦.

1152
V. N. Kozel et al.
FIGURE 3 Charge distribution and Wiberg indexes of compounds 1a and 2.
found to be 1.708 Å, and the sum of the angles at nitrogen is 337.9◦.)
On the other hand, the S-F bond length exceeds the corresponding
value found for Me-S-F (1.668 Å). Thus, some structural and spectral
properties are present, which make it possible to suggest a significant
contribution of the mesomeric form B to the structure of the molecules
1a,b. However, some other facts should also be taken into account.
The analysis of the charge distribution performed within the NBO ap-
proach shows that the N-S bond is highly polarized and hence possesses
an ylidic character. Important evidence to this interpretation is an in-
significant increase of the Wiberg index for the N-S bond compared
to the formally single bond. As expected, a significant negative charge
is localized at the fluorine atom; however its magnitude (–0.53) does
not directly prove the existence of 1a,b as the tight ion pair B. Thus,
the exceeded charge at the fluorine atom calculated for the sulfinic
acid derivative 2 is even larger (–0.56), whereas the δ19F values differ
strongly from those found for 1a,b (Figure 3). Therefore, the charge dis-
tribution itself is not the main reason of the strong shielding of the flu-
orine nuclei found for 1a,b. The calculation results for the synthesized
fluorides of the dialkylamino sulfoxylic acids and related compounds
as well as the character of the influence of their electronic structure
on the spectral characteristic will be considered in one of our future
publications.
The chemical properties of the dialkylamido sulfoxylic acid fluorides
1a,b have been studied by taking their reaction with unsaturated com-
pounds as an example. We have chosen cyclohexene, 3,4-dihydro-2H-
pyrane, and vinyl ethyl ether as substrates. In every case, the reaction
was performed in solution of anhydrous acetonitrile with cooling in an
ice bath (the reaction is exothermic). The products were purified by
distillation in high vacuum; partial tarring was observed (Scheme 3).
We attribute to the compound 3a trans-configuration with equato-
rial position of the fluorine and sulfur atoms (eFeS). This is confirmed

Dialkylamido Sulfoxylic Acid Fluorides
1153
SCHEME 3
3
by the values of vicinal coupling constants JH1 H2 (9 Hz) and 3JFH1 (10
Hz). Optimization of all possible structures for 3a shows that torsion
angles H1C1C2H2 and FC2C1H1 for the conformation 3a (eFeS)
(Figure 4) are 170.4◦ and –54.4◦, respectively, which agrees with the
experimental values on the basis of Karplus dependences for the values
of the corresponding coupling constants.10,11
It should be mentioned that only regioisomers 4 and 5, in which the
fluorine atom is bonded to the α-carbon atom, were formed in the case of
3,4-dihydro-2H-pyrane or vinyl ethyl ether. Compound 4a is obviously
a trans isomer with conformation (aFaS) (Figure 4). This is confirmed
3
by the small value of the vicinal coupling constant JFH2 (6.0 Hz). The
approximate value of the torsion angle FC1C2H2 corresponding to this
coupling constant and obtained by Karplus equation11 is about 58◦. For
the structure 4a (aFaS), optimized at the B3LYP/6-311++G∗∗ level of
theory (Figure 5), the mentioned angle is 65.3◦. This assignment agrees
with the values of full energies calculated for the corresponding iso-
mers [4a (aFaS) is characterized by lower full energy than 4a (eFeS),
Table I]. In addition the preferable equatorial position of the sub-
stituents in cyclohexanes and axial in tetrahydropyranes (in conse-
quence of the so called anomeric effect) is well documented in the
literature.11 Together with the main product 4a (aFaS), the cis-isomer
with suppositional conformation 4a (aFeS) is formed as a minor prod-
uct (about 9%) (Figure 4). The calculated full energy of the last one
is lower than in case of conformation 4a (eFaS), obviously due to
the mentioned above anomeric effect. The main argument in favor

1154
V. N. Kozel et al.
FIGURE 4 Conformational and stereoisomers of compounds 3 and 4.
of this structure is the high value of the vicinal coupling constant
3JFH2 (30.6 Hz), which should correspond to a value of the torsion an-
gle FC1C2H2close to 180◦.11 The mentioned value for the optimized
structure 4a (aFeS) is 171.3◦ (Figure 5). The absolute value of the con-
stant 3JH1 H2 (2.0 Hz) fits well to the theoretically calculated value of the

Dialkylamido Sulfoxylic Acid Fluorides
1155
TABLE I Total Energy (E), ZPE Correction, Corrected Energy Values
(Hartree), Lowest Vibration Frequencies Calculated for Different
Structures, and Relative Energy Magnitudes (kcal/mol) Calculated
(B3LYP/6–311++G∗∗) for 3a and 4a
Total
Energy, E
ZPE
correction
ꢀE,
Conformationa
E+ZPE
ν, cm−1 kcal/molb
trans-3a
trans-3a
cis-3a
(aFaS)
(eFeS)
(aFeS)
(eFaS)
(aFaS)
(eFeS)
(aFeS)
(eFaS)
–867.416871 0.235036 –867.181835
–867.417760 0.234906 –867.182854
–867.415587 0.234904 –867.180683
–867.416087 0.234841 –867.181246
–903.329231 0.211276 –903.117955
–903.326538 0.211037 –903.115501
–903.322612 0.210911 –903.111701
–903.329442 0.211227 –903.118215
23.1
23.2
25.1
28.2
23.3
23.2
21.0
26.0
0.6
0.0
1.4
1.0
0.2
1.7
0.0
4.1
cis-3a
trans-4a
trans-4a
cis-4a
cis-4a
aConformations with the NMe2 group oriented towards the ring possess higher
energies and are not considered here.
bBold marked values are referred to the most favored conformations for the cis- and
trans-isomers.
angle H1C1C2H2 (54.2◦) and its approximate evaluation by Karplus
equation.
It should be mentioned that in case of the compound 4b, a small
quantity of the cis-isomer is formed (< 1%).
The action of gaseous hydrogen chloride on 2-fluorocyclohexyl
sulfenic acid diisopropyl amide 3b leads to the cleavage of the S-N
bond and formation of 2-fluorocyclohexyl sulfenic acid chloride 6. Com-
pound 6 is a representative of the alkylsulfenyl chlorides of a new type,
as it contains a fluorine atom at the β-carbon atom.
In conclusion, we propose new reagents that allow the introduction
fluorine atoms in molecules of unsaturated aliphatic compounds form-
ing stereo- and regioselectively β-fluoroalkane sulfenic acid derivatives.
EXPERIMENTAL
Reagents and Materials
Reactions with compounds, sensitive to air and moisture, were con-
ducted in glassware and flame dried in a flow of dry argon using
anhydrous solvents in an atmosphere of dried argon. 1H and 19F NMR
spectra were recorded with a Varian VRX-300 spectrometer operating
at 299.9 MHz and 188.1 MHz, respectively. 13C NMR spectra were ob-
tained with a Bruker Avance 400 spectrometer operating at 100.62
1
MHz. Chemical shifts of the nuclei H and 13C are given in δ values

1156
V. N. Kozel et al.
FIGURE 5 Calculated (B3LYP/6-311++G**) most stable conformations of the
compounds 3à (eFeS), 4à (àFàS), and 4à (àFåS). The most important struc-
tural parameters (bond lengths in Å, angles in ◦): N-S 1.703, 1.713, 1.713;
C1-F 1.414, 1.424, 1.415; C2-S 1.873, 1.877, 1.868; NSC2 109.6, 105.3, 105.6;
H1C1C2H2 170.4, 65.3, 54.2; FC1C2H2 54.4, 51.2, 171.3, respectively.

Dialkylamido Sulfoxylic Acid Fluorides
1157
SCHEME 4
relatively to TMS as an internal standard. C6F6 (δ19F = –162.9 ppm
with respect to CFCl3) was used as an internal standard. “Spray-dried”
potassium fluoride of 99% purity was used for the reactions.
Details of Calculations
The structures were optimized using the GAUSSIAN-03 program set12
at the DFT (B3LYP13) and MP2 (with the frozen core approximation)
levels of theory. For the former case, the three-parameter hybrid func-
tional including Lee, Yang, and Parr14 and VWN515 functionals was
used. The geometry optimization was performed using 6-311+G∗∗ (for
the calculations at the MP2 level of approximation) or 6-311++G∗∗ (for
the DFT calculations) basis sets. Within the GAUSSIAN package, the
default usage of these basis sets meant Pople’s 6-311G basis sets16 for
hydrogen and second period atoms (C, N, O, F) and McLean-Chandler
basis set17 for sulfur, augmented with the corresponding polarization
and diffuse Gauss functions. In order to make sure that all the calcu-
lated structures corresponded to the local minima in energy, we per-
formed the vibration frequency analyses calculating analytically the
first and second derivatives. The optimized structures are presented
using the VMD program.18
Syntheses
Synthesis of Compounds 3a,b, 4a,b, and 5b: General
Procedure
Anhydrous KF (4.5 g, 77.4 mmol), 15 mL of acetonitrile, and dialky-
lamino sulfoxylic acid chloride (25.8 mmol) were placed into a flask with
a magnetic mixer anchor. The reaction mixture was stirred at room tem-
perature for 16 h. Volatile products were evaporated in vacuum (0.04
Torr) into a trap cooled by liquid nitrogen. The content of the trap (di-
alkylamido sulfoxylic acid fluoride and acetonitrile) was warmed to 0◦Ñ,
and alkene (2.12 g, 25.8 mmol) was added to the mixture with stirring
during 5 min. The reaction mixture was warmed to room temperature
during 1 h. The solvent was evaporated in vacuum (0.04 Torr), and the

1158
V. N. Kozel et al.
crude oily products were purified by vacuum distillation. The yields of
1
the crude products in all cases are close to quantitative based on H
and 19F NMR data.
2-Fluorocyclohexyl Sulfenic Acid Dimethylamide (3a)
Yield: 31.2%, b.p. 50–52◦C/0.04 Torr; 1H NMR (CDCl3/TMS): δ = 1.3
(m, 2H, cyclohexyl), 1.45–1.74 (m, 3H, cyclohexyl), 1.73 (m, 1H, cyclo-
3
hexyl), 2.1 (m, 2H, cyclohexyl), 2.74 (s, 6H, CH3), 2.85 (dddd, JHF
=
10.0 Hz, 3JH6a = 8.7 Hz, 3JH2a = 8.7 Hz, 3JH6e = 4.1 Hz, 1H, CHS), 4.44
(dddd, 1H, 2JHF = 48.6 Hz, JH1a = 8.9 Hz, 3JH3a = 8.9 Hz; 3JH3e = 4.2
3
Hz, CHF); 19F NMR (CDCl3/C6F6): δ = −171.07 (d, J = 45.3 Hz);13C
NMR (CDCl3): δ = 92.7 (d, J = 176.0 Hz, C-2), 50.4 (Me), 50.2 (d, J =
24.8 Hz, C-1), 31.7 (d, J = 19.8 Hz, C-3), 30.0 (d, J = 4.4 Hz, C-6), 25.0
(C-5), 23.3 (d, J = 8.7 Hz, C-4). Calcd for C8H16FNS (177.28): C, 54.20;
H, 9.10; F, 10.72; N, 7.90; S, 18.09. Found: C, 54.00; H, 8.85; F, 10.84;
N, 7.78; S, 18.02%.
2-Fluorocyclohexyl Sulfenic Acid Diisopropylamide (3b)
1
Yield: 62.6%, b.p. 67–70◦C / 0.03 Torr; H NMR (CDCl3/TMS): δ =
1.09 (dd, J = 6.6 Hz, 2.1 Hz, 12H, CH3), 1.3–1.8 (m, 6H, cyclohexyl),
3
3
2.0–2.2 (m, 2H, cyclohexyl), 2.71 (dddd, JH2a = 9.7 Hz, JHF = 9.5
3
3
Hz, JH6a = 9.5 Hz, JH6e = 4.5 Hz, 1H, CHS), 3.22 (sept, J = 6.5 Hz,
2
3
3
2H, CH), 4.49 (dddd, JHF = 48.6 Hz, JH1a = 7.8 Hz, JH3a = 7.8 Hz;
3JH3e = 3.9 Hz, 1H, CHF);19F NMR (CDCl3/C6F6): δ = −173.1 (d, J =
48.7 Hz);13C NMR (CDCl3): δ = 93.2 (d, J = 175.5 Hz, C-2), 55.6 (d,
J = 16.4 Hz, C-1), 54.1 (CH), 31.0 (d, J = 19.8 Hz, C-3), 28.8 (d, J =
3.8 Hz, C-6), 24.3 (C-5), 23.8 (CH3), 22.8 (d, J = 8.2 Hz, C-4). Calcd
for C12H24FNS (233.37): C, 61.75; H, 10.36; F, 8.14; N, 6.00; S, 13.74.
Found: C, 62.01; H, 10.33; F, 7.76; N, 6.12; S, 14.12%.
2-Fluorotetrahydro-2H-pyrane-3-sulfenic Acid
Diisopropylamide (4b)
Yield: 33%, b.p. 65–67◦C / 0.03 Torr;1H NMR (CDCl3/TMS): δ = 1.08
(d, J = 6.6 Hz, 12H, CH3), 1.42 (m, 1H, CH2CHS), 1.85 (t, J = 15.3 Hz,
2H, CH2CH2CH2), 2.12 (m, 1H, CH2CHS), 2.82 (s, 1H, CHS), 3.20 (sept,
J = 6.5 Hz, 2H, CH), 3.70 (m, 1H, CH2O), 3.91 (td, J = 11.1 Hz, 2.1 Hz,
1H, CH2O), 5.67 (d, 2JHF = 52.8 Hz, 1H, CHF); 19F NMR (CDCl3/C6F6):
δ = −129.3 (d, J = 52.5 Hz); 13C NMR (CDCl3): δ = 108.3 (d, J = 220.5
Hz, C-1), 62.1 (d, J = 3.2 Hz, C-5), 55.1 (CH), 51.0 (d, J = 23.9 Hz, C-2),
23.4 (CH3), 21.8 (C-3), 21.1 (C-4). Calcd for C11H22FNOS (235.36): C,
56.13; H, 9.42; F, 8.07; N, 5.95; S, 13.62. Found: C, 56.20; H, 9.50; F,
7.75; N, 6.23; S, 13.59%.

Dialkylamido Sulfoxylic Acid Fluorides
1159
2-Ethoxy-2-Fluoroethyl Sulfenic Acid Diisopropylamide (5b)
Yield: 21%, b.p. 50–55◦C / 0.07 Torr;1H NMR (CDCl3/TMS): δ = 1.10
(d, J = 6.6 Hz, 12H, CH3CH), 1.25 (t, J = 6.9 Hz, 3H, CH3), 2.78 (m,
1H, SCH2), 2.82 (m, 1H, SCH2), 3.21 (sept, J = 6.5 Hz, 2H, CH), 3.78
(d, J = 71.1 Hz, OCH2), 5.41 (dt, J = 66.9 Hz, 5.25 Hz, -CHF-);19F NMR
(CDCl3/C6F6): δ = −121.64 (dt, J = 66.0 Hz, 14.9 Hz); 13C NMR (CDCl3):
δ = 111.6 (d, J = 215.7 Hz, CF), 65.8 (CH2O), 55.9 (CH), 47.3 (d, J =
22.6 Hz, CH2S), 23.7 (CHCH3), 15.4 (CH2CH3). Calcd for C10H22FNOS
(223.35): C, 53.77; H, 9.93; F, 8.51; N, 6.27; S, 14.36. Found: C, 53.68;
H, 9.93; F, 8.15; N, 6.76; S, 14.38%.
Trans-2-fluorotetrahydro-2H-pyrane-3-sulfenic Acid
Dimethylamide (4a, aFaS)
Yield: 43%, b.p. 57–60◦C / 0.04 Torr; 1H NMR (CDCl3/TMS): δ = 1.47
(m, 1H, CH2CHS), 1.78 (m, 2H, CH2CH2CH2), 2.23 (m, 1H, CH2CHS),
2.72 (s, 6H, CH3), 3.21 (s, 1H, CHS), 3.71 (m, 1H, CH2O), 3.94 (m, 1H,
2
3
CH2O), 5,63 (dd, JHF = 52.8 Hz, JH2e = 5.8 Hz, 1H, CHF); 19F NMR
(CDCl3/C6F6): δ = −127.07 (dd, J = 52.5 Hz, 6.0 Hz);13C NMR (CDCl3):
δ = 108.6 (d, J = 222.6 Hz, C-1), 62.3 (d, J = 3.3 Hz, C-5), 49.6 (Me),
43.7 (d, J = 25.2 Hz, C-2), 23.3 (C-3), 21.6 (C-4). Calcd for C7H14FNOS
(179.26): C, 46.90; H, 7.87; F, 10.60; S, 17.89. Found: C, 46.84; H, 7.76;
F, 10.56; S, 17.66%.
Cis-2-fluorotetrahydro-2H-pyrane-3-sulfenic Acid
Dimethylamide (4a, aFeS)
2
3
19F NMR (CDCl3/C6F6): δ = −146.9 (dd, JH1e = 51.4 Hz, JH2a
=
30.6 Hz);13C NMR (CDCl3): δ = 107.6 (d, J = 220.2 Hz, C-1), 61.6 (d,
J = 3.7 Hz, C-5), 49.9 (Me), 46.1 (d, J = 27.6 Hz, C-2), 25.6 (C-3), 23.9
(C-4).
2-Fluorocyclohexyl Sulfoxylic Acid Chloride (6)
Hydrogen chloride (6.24 g, 171.2 mmol) is passed into a solution of 2-
fluorocyclohexyl sulfenic acid diisopropylamide 3b (2.0 g, 8.56 mmol) in
diethyl ether (20 mL). The colorless crystalline precipitate was filtered
and the filtrate was evaporated in vacuum. 2-Fluorocyclohexyl sulfenic
acid chloride 6 remained in the residue and was purified by distillation
in vacuum. Yield: 81%, b.p. 55◦C / 0.07 Torr; 1H NMR (CDCl3/TMS): δ =
1.3–1.4 (m, 2H, cyclohexyl), 1.5–1.85 (m, 4H, cyclohexyl), 2.1–2.3 (m,
2H, cyclohexyl), 3.05 (dddd, 3JF = 10.7 Hz, 3JH2a = 8.5 Hz; 3JH6a = 8.0
3
2
3
Hz; JH6e = 4.2 Hz, 1H, CHS), 4.5 (dddd, JHF = 48.0 Hz, JH1a = 9.5
3
3
Hz, JH3a = 9.5 Hz, JH3e = 4.7 Hz, 1H, CHF).19F NMR (CDCl3/C6F6):
δ = −173.1 (d, J = 48.7 Hz). Calcd for C6H10ClFS (168,66): C, 42.73; H,

1160
V. N. Kozel et al.
5.98; F, 11.26; S, 19.01; Cl, 21.02. Found: C, 42.70; H, 5.99; F, 9.56; S,
19.17; Cl, 21.08%.
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