Chromatography-mass spectrometry studies of transarylation and disproportionation reactions of diaryl telluroxides

Article abstract of DOI:10.1007/s11172-017-1784-x

Electrospray ionization chromatography-mass spectrometry was used to study transarylation and disproportionation reactions of di(4-methoxyphenyl) and di(4-dimethylaminophenyl) telluroxides in refluxing toluene. The reaction mixture compositions were estab

Full text of DOI:10.1007/s11172-017-1784-x

Russian Chemical Bulletin, International Edition, Vol. 66, No. 4, pp. 636—642, April, 2017
636
Chromatographyꢀmass spectrometry studies of transarylation
and disproportionation reactions of diaryl telluroxides
E. V. Eliseeva,a N. A. Red´kin,a V. P. Gar´kin,a I. S. Pytskii,b and A. K. Buryakb
aS. P. Korolev Samara National Research University,
34 Moskovskoe shosse, 443086 Samara, Russian Federation.
Eꢀmail: eveletskaya@gmail.com
bA. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences,
Korp. 4, 31 Leninsky prosp., 119071 Moscow, Russian Federation
Electrospray ionization chromatographyꢀmass spectrometry was used to study transarylaꢀ
tion and disproportionation reactions of di(4ꢀmethoxyphenyl) and di(4ꢀdimethylaminophenyl)
telluroxides in refluxing toluene. The reaction mixture compositions were established based on
the mass spectrometry data and relative retention times. General schemes for fragmentation of
the reaction mixture components were suggested.
Key words: chromatographyꢀmass spectrometry, electrospray ionization, tandem mass
spectrometry, diaryl telluroxide, diaryl telluride, triaryltelluronium ion, aryloxytriaryltelluꢀ
rane, disproportionation, transarylation.
Chromatographyꢀmass spectrometry is widely used in
sults of the gas chromatography studies of diaryl telluroxꢀ
ides with mass spectrometric detection allowed one to
draw a conclusion that heating a mixture of symmetric
diaryl telluroxides led to the formation of unsymmetric
compounds of this class and disproportionation of the
starting compounds is possible. Earlier,13,14 chromatograꢀ
phyꢀmass spectrometry study of the reactions of formaꢀ
tion of unsymmetric diaryl telluroxides has been carried
out upon heating a mixture of symmetric diaryl tellurꢀ
oxides for 2 h at 100 °C in a sealed quartz tube. However,
some side products were not identified.
different areas of science and technique,1 in particular, in the
study of mechanisms of organic reactions and identificaꢀ
tion of synthesized products. For labile compounds, it is
important to use "mild" ionization, allowing transition of
such molecules into the gas phase without decomposition.
Electrospray ionization mass spectrometry (ESIꢀMS) is
one of the variants of "mild" ionization. Tandem mass
spectrometry (ESIꢀMS/MS) is used to increase the reliꢀ
ability of identification. An important supplementation to
mass spectrometric identification is chromatographic
identification based on the use of chromatographic retenꢀ
tion time values.2,3 These methods were used earlier for
the studies of mechanisms of different organic reactions,
including those involving organotellurium compounds.4—6
A number of works were devoted to the reactions of
inorganic and organic derivatives of diꢀ and tetracoordiꢀ
nated tellurium as reagents and catalysts. Reaction pathꢀ
ways of tellurium tetrachloride and aryltellurium trichloride
with alkynes were investigated.5,7 Using ESIꢀMS/MS, it
was found out that during bromination of different organic
compounds in the presence of diaryl ditellurides in cataꢀ
lytic amounts the diaryl ditellurides underwent oxidation by
hydrogen peroxide with the formation of the correspondꢀ
ing aryltelluronium acids, which acted as the catalysts.8
Mass spectrometry and chromatographyꢀmass spectroꢀ
metry studies of diaryl telluroxides and other organotelluriꢀ
um compounds allowed one to identify specific features of
analysis of individual diaryl telluroxides and their model
mixtures under conditions of liquid9,10 and gas chromaꢀ
tography11,12 with mass spectrometric detection. The reꢀ
Experimental
Diaryl telluroxides were synthesized at the Department of
Analytical and Expert Chemistry of the S. P. Korolev Samara
National Research University according to the known proceꢀ
dures.15
Preparation of reaction mixtures. The reaction mixtures were
obtained by the disproportionation and transarylation reactions
of di(4ꢀmethoxyphenyl)ꢀ and di(4ꢀdimethylaminophenyl) tellurꢀ
oxide (Table 1) upon reflux of the starting reagents (0.1 mmol) in
toluene for 4 h using a reflux condenser.
Chromatographyꢀmass spectrometry study of the reaction mixꢀ
ture compositions. Chromatographic separation of components of
reaction mixtures was carried out on an Agilent Technologies 1260
Infinity liquid chromatograph with a Bruker Maxis Impact mass
spectrometric detector, a ZORBAX SBꢀC18 column (2.1×150 mm,
3.5 μm), electrospray ionization (ESI). The column thermostat
temperature was 45 °C. A fourꢀcomponent mixture of solvents
water—methanol—acetonitrile (50 : 40 : 10) with addition of
0.05% of trifluoroacetic acid (TFAA) (phase A) and pure acetoꢀ
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0636—0642, April, 2017.
1066ꢀ5285/17/6604ꢀ0636 © 2017 Springer Science+Business Media, Inc.

HPLCꢀMS of diaryl telluroxides transarylation
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 4, April, 2017
637
Table 1. Starting reagents for the preparation of reaction mixtures
collisions was 10 eV. The experimental m/z values were comꢀ
pared with the m/z values calculated using the IsoPro 3.0 software.
Reaction
mixture
Starting reagent
Reaction
Results and Discussion
1
2
3
Di(4ꢀmethoxyphenyl)
telluroxide
Di(4ꢀdimethylaminophenyl)
telluroxide
Di(4ꢀmethoxyphenyl)
telluriumoxide
Di(4ꢀdimethylaminophenyl)
telluroxide
Disproporꢀ
tionation
Disproporꢀ
tionation
Chromatographyꢀmass spectrometry studies of starting
compounds. To confirm the absence of impurities which can
interfere with the determination of the reaction mixture
compositions, we carried out chromatographyꢀmass spectroꢀ
metry examination of the starting compounds. The retenꢀ
tion times of di(4ꢀmethoxyphenyl) and di(4ꢀdimethylꢀ
aminophenyl) telluroxide were found to be 1.2 and 1.8 min,
respectively. Therefore, this parameter can be used for the
identification of these compounds.
Transarylation
Disproporꢀ
tionation
nitrile with addition of 0.05% of TFAA (phase B) were used as
mobile phases. The following gradient of eluents was used: first
three minutes phase A, from 4th to 10th min phase B, from 11th
to 15th min phase A. These conditions of chromatographic sepaꢀ
ration were found to be the most acceptable for the analysis of
studied reaction mixtures after variation of parameters.
Under the ESI mass spectrometry conditions, di(4ꢀ
methoxyphenyl) and di(4ꢀdimethylaminophenyl) telluroxꢀ
ides form protonated molecules, which have the maxiꢀ
mum signal intensities (Fig. 1). Apart from that, the mass
spectra of these compounds exhibit ions, the structure of
which corresponds to diaryl tellurides [M – O]+, diaryls
[Ar + Ar]+, dimers [2 M + H]+, associates with the comꢀ
ponents of mobile phases [M + H + MeOH – H2O]+,
[M + H + CF3COOH – H2O]+, [2 M + H + CF3COOH –
– H2O]+. The obtained m/z values of ions agree with the
calculated values. Under ESI conditions, the diaryl telꢀ
luroxide ions are formed following the same scheme
(Scheme 1), which can serve as an additional indication of
identification in the determination of other representaꢀ
tives of organotellurium compounds under consideration.
Chromatographyꢀmass spectrometry study of disproporꢀ
tionation reaction. Earlier,13,14 when studying the influence
of high temperatures on binary mixtures of diaryl tellurꢀ
The reaction mixtures were injected into chromatograph
without dilution (in toluene) in the amount of 1 μL.
Mass spectrometry detection of the reaction mixture comꢀ
ponents was carried out in the positive ion mode in the range
m/z = 50—3000 at a capillary and a counter electrode voltage of
3500 and 500 V, respectively . The flow rate was 4.5 L min–1, the
temperature of nitrogen was 250 °C. The registration rate was
four spectra per 1 s. The structure of products formed in disproꢀ
portionation and transarylation was studied using MS/MSꢀspecꢀ
trometry by scanning a certain m/z range and the choice of
a required ionꢀprecursor, subsequent dissociation of the ionꢀ
precursor upon collision with nitrogen molecules in the collision
cell and TOFꢀanalysis of masses of resulting ions. The ion transꢀ
mission band value of chosen ions Δm/z = 11. The energy of
[M + H]+
361
I (arb. units)
a
1.5
1.0
[M + H + CH3OH – H2O]+
375
0.5
[2 M + H + CF3COOH – H2O]+
[(C7H7O)2]+
214
[M + H + CF3COOH – H2O]+
475
[M – O]+
344
813
[2 M + H]+
717
100
I (arb. units)
200
300
400
500
600
700
800
m/z
[M + H]+
387
b
1.25
1.00
0.75
0.50
0.25
[M + H + CH3OH – H2O]+
401
[M – C7H10N + H]+
267
[2 M + H + CF3COOH – H2O]+
865
[(C8H10N)2]+
240
[2 M + H]+
769
[M + H + CF3COOH – H2O]
483
100
200
300
400
500
600
700
800
m/z
Fig. 1. Mass spectra of di(4ꢀmethoxyphenyl) (a) and di(4ꢀdimethylaminophenyl) telluroxide (b).

638
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 4, April, 2017
Eliseeva et al.
Scheme 1
oxides we detected formation of products, the structure of
which was not established. We suggested that diaryl tellurꢀ
oxides treated with heat underwent disproportionation. To
confirm a possibility of this process, we carried out chromꢀ
atographyꢀmass spectrometry studies of the reaction mixtures
(Fig. 2) obtained by heating individual diaryl telluroxides.
From the recorded chromatographic patterns, it folꢀ
lows that the reaction mixture 1 contains two compoꢀ
nents, while the reaction mixture 2 is composed of four
components. Based on the retention time values (tR) and
mass spectra, we identified the starting di(4ꢀmethoxyꢀ
phenyl) telluroxide (tR = 1.3 min) and di(4ꢀdimethylꢀ
aminophenyl) telluroxide (tR = 2.1 min). The structures
of other components of the reaction mixtures under study
were inferred from the mass spectrometry data (Table 2).
We found that fragment ions are practically absent in
the mass spectra of the second peak in the chromatoꢀ
graphic pattern of the reaction mixture 1 and of the forth
peak in the chromatographic pattern of the reaction mixꢀ
ture 2, the structure of the most abundant ions supposedly
corresponds to triaryltelluronium ions [Ar3Te]+.
It is known that triaryltelluronium ions exist as salts.
However, their formation under the studied reaction conꢀ
ditions is impossible. According to the literature data,

HPLCꢀMS of diaryl telluroxides transarylation
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 4, April, 2017
639
I ( arb. units )
3.6
a
3
2
1
1.3
1
2
3
4
5
6
7
tR/min
I ( arb. units )
b
5.1
2.5
2.0
1.5
1.0
0.5
2.1
4.8
0.8
1
2
3
4
5
6
7
tR/min
Fig. 2. Mass chromatograms of the reaction mixtures 1 (a) and 2 (b) for the main ions.
derivatives of tetracoordinated tellurium do not form staꢀ
ble molecular ions. The desorption chemical ionization
mass spectrometry data for TeIV alkoxy derivatives are
considered in the work.16 One of the compounds, namely,
ethoxytriphenyltellurane, is characterized by the absence
in the mass spectrum of a molecular ion. The fragmentaꢀ
tion of its protonated molecular ion is accompanied by
elimination of a protonated alkoxy group with the formaꢀ
tion of the Ph3Te+ ion.
Thus, it was suggested that the heating of diaryl telꢀ
R = —OMe, —NMe2
luroxides under study led to the formation of (4ꢀmethꢀ
oxyphenoxy)tri(4ꢀmethoxyphenyl)tellurane and (4ꢀdiꢀ
methylaminophenoxy)tri(4ꢀdimethylaminophenyl)tellurꢀ
ane, the structures of which are shown in the text below.
To confirm the structures of disproportionation prodꢀ
ucts, we studied the principal directions of fragmentation
of triaryltelluronium ions under the ESIꢀMS/MS condiꢀ
tions. It was found that in the MS/MS spectra, the peaks
of the most abundant ions correspond to diaryls. The ions
with the structure of diaryl tellurides and aryl tellurides
give peaks with low intensities. The molecular formulas of
ions were found by the comparison of the experimental
m/z values with the calculated data. The principal direcꢀ
tions of fragmentation of triaryltelluronium ions are given
in Scheme 2.
The results of the MS/MS spectroscopy study are conꢀ
firmed by the literature data. Under the desorption chemꢀ
ical ionization conditions, ethoxytriphenyltellurane is
characterized by the formation of the Ph2Te+• and PhTe+
ions.16 The studies17 of tellurium tetrachloride by ESI mass
spectrometry showed that the most abundant peak correꢀ
sponds to the structure of TeCl3+. The MS/MS spectrum
obtained for this ion contained the peaks of the [TeCl2]+
and [TeCl]+ ions formed by sequential elimination of
a chlorine atom.
Table 2. Retention times and main ions in the mass spectra of the
reaction mixture components
Reacꢀ
tion
mixture
tR
m/z
Structure of ion
corresponding to the most
abundant peak
/min of main
ion
1
2
1.3 361.0109
3.6 451.0616
0.8 122.0976
2.1 387.0742
4.8 371.0791
[(pꢀMeOC6H4)2TeO + H]+
[(pꢀMeOC6H4)3Te]+
[Me2NPh + H]+
The reaction mixture 2 is distinguished by the presence
of a larger number of disproportionation products. The
retention time of the first component corresponds to
N,Nꢀdimethylaniline. The mass spectrum does not exhiꢀ
[(pꢀMe2NC6H4)2TeO + H]+
[(pꢀMeOC6H4)2Te + H]+
+
5.1 490.1513 [(pꢀMeOC6H4)Te(pꢀMe2NC6H4) + H
]

640
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 4, April, 2017
Eliseeva et al.
Scheme 2
bit peaks of telluriumꢀcontaining ions, while the main
peak corresponds to the structure of the protonated moleꢀ
cule [(C8H11N) + H]+ with m/z 122.0976.
The massꢀchromatographic pattern also contains
a component with the retention time of 4.8 min. The strucꢀ
ture of the corresponding compound was inferred from the
mass spectrum and the MS/MS spectrum.
The most abundant ion in the mass spectrum (Fig. 3)
corresponds to the protonated molecule of di(4ꢀdimethylꢀ
aminophenyl) telluride [M + H] with m/z 371.0789. Apart
from that, the mass spectrum exhibits peaks for the folꢀ
lowing ions: [(C8H10N)2 + H – Me]+ with m/z 226.1507,
[M + H – M] with m/z 356.0550, and [M + (C8H10N)Te]+
with m/z 618.0555. The presence of a signal for the ion
with m/z 490 in the mass spectrum is related to the insuffiꢀ
cient efficiency of chromatographic separation of two comꢀ
ponents of the reaction mixture. This signal belongs to the
mass spectrum of (4ꢀdimethylaminophenoxy)tri(4ꢀ
dimethylaminophenyl)tellurane. Under the tandem mass
spectrometry conditions, di(4ꢀdimethylaminophenyl) telꢀ
luride practically does not form fragment ions. The most
abundant peak in the MS/MS spectrum corresponds to
the [(C8H10N)2 + H – Me]+ ion.
massꢀchromatographic patterns of the reaction mixture 3
(Fig. 4) revealed the presence of ten components. Despite
the insufficient efficiency of separation of the reaction
mixture components under the applied chromatographic
conditions, the identification is possible based on the mass
spectrometry data.
The retention time values and the mass spectrometry
and MS/MS data showed the presence in the reaction
mixture 3 of the starting diaryl telluroxides and the prodꢀ
ucts of their disproportionation. The structures of other
components of the reaction mixture were inferred from
mass and MS/MS spectra (Table 3).
4ꢀDimethylaminophenyl 4ꢀmethoxyphenyl telluroxide
(Fig. 5) formed by transarylation was identified using
a mass spectrum of the third peak.
In the mass spectrum of 4ꢀdimethylaminophenyl
4ꢀmethoxyphenyl telluroxide (see Fig. 5), the most abunꢀ
dant signal corresponds to the protonated molecule
[M + H]+ with the m/z equal to 374.0376. This mass specꢀ
trum contains the following ion peaks: [M + H + MeOH –
– H2O]+, m/z 388.0540; [M + H + CF3COOH – H2O]+,
m/z 470.0226; [2 M + H]+, m/z 745.0656; [2 M + H +
+ CF3COOH – H2O]+, m/z 841.0522; [(C7H7O) +
+ (C8H10N)]+, m/z 227.1330. The ion m/z values agree
with the calculation results. The principal directions of
the ion formation under the HPLC/MSꢀESI conditions
correspond to the general Scheme 1.
Based on the chromatographyꢀmass spectrometry studꢀ
ies of the reaction mixtures obtained by reflux of each of
the diaryl telluroxides in toluene, it was found that di(4ꢀ
methoxyphenyl) and di(4ꢀdimethylaminophenyl) telluroxꢀ
ides undergo disproportionation.
The main ions in the mass spectra of the seventh and the
eighth peaks are the nonsymmetric triaryltelluronium ions
Ar´2Ar″Te+ (Ar´ = pꢀMeO(C6H4), Ar″ = pꢀMe2N(C6H4),
Chromatographyꢀmass spectrometry study of transarylꢀ
ation reaction. The examination of the main ions in the
[M + H]+
371
I (arb. units)
1.0
0.8
0.6
0.4
[(C8H10N)3Te]+
490
[(C8H10N)2 + H — CH3]+
[M + (C8H10N)Te]+
616
[M + H — CH3]+
356
0.2
226
100
200
300
400
500
600
m/z
Fig. 3. Mass spectrum of di(4ꢀdimethylaminophenyl) telluride.

HPLCꢀMS of diaryl telluroxides transarylation
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 4, April, 2017
641
I (arb. units)
4.8
5.0
2.5
5.1
1.5
2.0
3.5
1.5
2.0
1.3
5.1
0.7
1.0
0.5
0
4.3
1
2
3
4
5
tR/min
Fig. 4. Mass chromatogram of the reaction mixture 3 for the main ions.
[M + H]+
374
I (arb. units )
1.5
[M + H + CH3OH – H2O]+
388
1.0
0.5
[2 M + H + CF3COOH – H2O]+
839
[C7H7O + C8H10N]+
227
[M + H + CF3COOH – H2O]+
470
[2 M + H]+
743
100
200
300
400
500
600
700
800
m/z
Fig. 5. Mass spectrum of 4ꢀdimethylaminophenyl 4ꢀmethoxyphenyl telluroxide.
m/z 464; Ar´ = pꢀMe2N(C6H4), Ar″ = pꢀMeO(C6H4),
m/z 477). The fragmentation of the indicated ions regisꢀ
tered in the MS/MS spectra occurs according to the genꢀ
eral fragmentation scheme (see Scheme 2), that additionꢀ
ally confirms their structure.
Thus, it can be suggested that these components are
nonsymmetric aryloxytriaryltelluranes: 4ꢀdimethylamiꢀ
nophenyl(4ꢀdimethylaminophenoxy)di(4ꢀmethoxyphenꢀ
yl)tellurane and di(4ꢀdimethylaminophenyl)(4ꢀmethoxyꢀ
phenyl)(4ꢀmethoxyphenoxy)tellurane. The presence of
these compounds in the reaction mixture 3 results from
the disproportionation of nonsymmetric diaryl telluroxide
formed by transarylation.
The mass spectrum of the tenth peak (Fig. 6) exhibits
two peaks of the telluriumꢀcontaining ions with m/z 358
and 490. Both signals are characterized by considerable
intensity. This fact indicates the presence of two different
components, which are eluted simultaneously under the
conditions used.
The ion with the m/z 358.0442 corresponds to the proꢀ
tonated molecule of 4ꢀdimethylaminophenyl 4ꢀmethꢀ
oxyphenyl telluride. Apart from that, this mass spectrum
exhibits the signals of the ions the structure of which is
identical to those formed by the fragmentation of di(4ꢀ
dimethylaminophenyl) telluride: [(C8H10N)(C7H7O) + H –
– Me]+ with m/z 213.1165 and [M + H – Me] with
m/z 343.0222. An additional confirmation of the structure
of nonsymmetric diaryl telluride is the presence in the
MS/MS spectrum of the most abundant peak of the ion
[(C8H10N)(C7H7O) + H – Me]+.
Table 3. Composition of the reaction mixture obtained in the
transarylation reaction
tR
/min
Structure of ion corresponding
to the most abundant signal
m/z of main
ions
0.7
1.3
1.5
N,NꢀDimethylaniline
Di(4ꢀmethoxyphenyl) telluroxide
4ꢀDimethylaminophenyl
122.0979
361.0077
374.0376
4ꢀmethoxyphenyl telluroxide
Di(4ꢀdimethylaminophenyl) telluroxide
(4ꢀMethoxyphenoxy)triꢀ
2.0
3.5
387.0695
451.0574
(4ꢀmethoxyphenyl)tellurane
Di(4ꢀdimethylaminophenyl) telluride
(4ꢀDimethylaminophenoxy)diꢀ
(4ꢀmethoxyphenyl)ꢀ
4.3
4.8
371.0770
464.0903
(4ꢀdimethylaminophenyl)tellurane
(4ꢀMethoxyphenoxy)diꢀ
5.0
477.1221
(4ꢀdimethylaminophenyl)ꢀ
(4ꢀmethoxyphenyl)tellurane
(4ꢀDimethylaminophenoxy)triꢀ
(4ꢀdimethylaminophenyl)tellurane
4ꢀDimethylaminophenyl
5.1
5.1
490.1509
358.0442
In conclusion, we carried out chromatographyꢀmass
spectrometry studies of disproportionation reactions of
di(4ꢀmethoxyphenyl) and di(4ꢀdimethylaminophenyl)
telluroxides. It was found that the disproportionation leads
4ꢀmethoxyphenyl telluride

642
Russ. Chem. Bull., Int. Ed., Vol. 66, No. 4, April, 2017
Eliseeva et al.
[M + H]+
358
I (arb. units)
4
3
2
1
[(C8H10N)3Te]+
490
[(C8H10N)(C7H7O) + H – CH3]+
213
[M + H – CH3]+
343
200
250
300
350
400
450
500
m/z
Fig. 6. Mass spectrum of 4ꢀdimethylaminophenyl 4ꢀmethoxyphenyl telluride.
5. L. S. Santos, Eur. J. Org. Chem., 2008, 235.
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to the formation of aryloxytriaryltelluranes. The disproꢀ
portionation of di(4ꢀdimethylaminophenyl) telluroxide is
characterized by the formation of not only aryloxytriarylꢀ
tellurane, but also of diaryl telluride.
The study of transarylation reaction of diaryl tellurꢀ
oxides showed the presence of nonsymmetric diaryl tellurꢀ
oxide in the reaction mixture. According to the mass
spectrometry and MS/MS data, in this case a parallel
disproportionation reaction of the starting reagents and
a transarylation of the reaction product with the formation
of symmetric and nonsymmetric aryloxytriaryltelluranes
occur. The disproportionation of nonsymmetric diaryl telꢀ
luroxide proceeds similarly to disproportionation of di(4ꢀ
dimethylaminophenyl) telluroxide, since a corresponding
diaryl telluride was found in the reaction mixture.
Based on the analysis of the results of mass spectroꢀ
metry and MS/MS studies, a general scheme for the forꢀ
mation of ions of diaryl telluroxides under the HPLC/
MSꢀESI conditions was suggested, as well as a scheme of
the fragmentation of aryloxytriaryltelluranes under tanꢀ
dem mass spectrometry conditions.
10. A. A. Sorokin, V. P. Gar´kin, N. A. Red´kin, A. K. Buryak,
Russ. J. Appl. Chem., 2010, 83, 2163.
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Chromatographic Processes], 2007, 37 (in Russian).
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Sorbtsionnye i khromatograficheskie protsessy [Sorption and
Chromatographic Processes], 2007, 244 (in Russian).
13. T. A. Rodina, Ph. D. (Chem.), A. N. Frumkin Institute of
Physical Chemistry and Electrochemistry of the Russian
Academy of Sciences, Moscow, 2009, 191 pp. (in Russian).
14. N. A. Red´kin, Ph. D. (Chem.), Samara State Univ., Samaꢀ
ra, 2008, 150 pp. (in Russian).
15. I. D. Sadekov, A. A. Maksimenko, V. I. Minkin, Khimiya
tellurorganicheskikh soedinenii [Chemistry of Organotellurium
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pp. (in Russian).
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