Reactions of chloromethyl heptyl ether with selenium and tellurium in the system hydrazine hydrate-potassium hydroxide

Article abstract of DOI:10.1134/S1070428011120049

Chloromethyl heptyl ether reacts with selenium in the system hydrazine hydrate-potassium hydroxide with formation of a mixture of bis(heptyloxymethyl) selane (32%) and bis(heptyloxymethyl)diselane (64%). Reductive cleavage of the latter with hydrazine hydrate-KOH and subsequent alkylation with methyl iodide gave methyl(heptyloxymethyl)selane in 94% yield. Analogous reaction of tellurium with hydrazine hydrate-KOH leads to the formation of extremely unstable bis(heptyloxymethyl)ditellane and bis(heptyloxymethyl) tellane at a ratio of 1: 4.

Full text of DOI:10.1134/S1070428011120049

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 12, pp. 1802–1806. © Pleiades Publishing, Ltd., 2011.
Original Russian Text © E.P. Levanova, V.A. Grabel’nykh, N.V. Russavskaya, A.I. Albanov, I.B. Rozentsveig, N.A. Korchevin, 2011, published in Zhurnal
Organicheskoi Khimii, 2011, Vol. 47, No. 12, pp. 1766–1770.
Dedicated to Full Member of the Russian Academy of Sciences
M.G. Voronkov on his 90th anniversary
Reactions of Chloromethyl Heptyl Ether with Selenium
and Tellurium in the System Hydrazine Hydrate–
Potassium Hydroxide
E. P. Levanova, V. A. Grabel’nykh, N. V. Russavskaya, A. I. Albanov,
I. B. Rozentsveig, and N. A. Korchevin
Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
e-mail: venk@irioch.irk.ru
Received April 6, 2011
Abstract—Chloromethyl heptyl ether reacts with selenium in the system hydrazine hydrate–potassium
hydroxide with formation of a mixture of bis(heptyloxymethyl)selane (32%) and bis(heptyloxymethyl)diselane
(64%). Reductive cleavage of the latter with hydrazine hydrate–KOH and subsequent alkylation with methyl
iodide gave methyl(heptyloxymethyl)selane in 94% yield. Analogous reaction of tellurium with hydrazine
hydrate–KOH leads to the formation of extremely unstable bis(heptyloxymethyl)ditellane and bis(heptyloxy-
methyl)tellane at a ratio of 1:4.
DOI: 10.1134/S1070428011120049
The chemistry of organoselenium and organotel-
lurium compounds has vigorously developed over past
decades. This is the result of continuous extension of
the scope of their application in technics [1], biology
[2], and especially in organic synthesis [3]. A new
impetus to the development of that field of organo-
element chemistry was given by studies on so-called
quantum points, i.e., nanoparticles of semiconducting
chalcogenide materials for which organochalcogen
compounds can act as stabilizing ligands [4]. The
stabilizing efficiency of ligands and parameters of
nanoparticles are largely determined by the hydro-
phobic–hydrophilic balance of the ligand residue.
groups (two halogen atoms) at the same carbon atom
are contradictory. For instance, reactions of methylene
chloride with polysulfide [5] and polyselenide anions
[6] in the system hydrazine hydrate–alkali gave oligo-
meric poly(methylenepolychalcogenides). Likewise,
methylene bromide reacted with aqueous sodium di-
selenide to produce poly(methylenediselane) [7]. How-
ever, in the reactions of methylene chloride [8] and
1,1-dichloroethane [9] with tellurium in hydrazine
hydrate–alkali, apart from products of nucleophilic
replacement of chlorine by tellurium, methyl- and
ethyltellanyl derivatives were obtained as a result of
partial reduction. Methylsulfanyl derivatives were also
formed in electrochemical synthesis of sulfides with
the use of methylene chloride [10], whereas the syn-
thesis of organoselenium compounds from benzylidene
chloride and selenium in the presence of sodium
hydride was accompanied by formation of up to 10%
of dibenzyldiselane [11]. Although ether group is
a weak nucleofuge, replacement of the butoxy group in
butyl diethylaminomethyl ether by the action of chal-
cogen derivatives of Grignard compounds ArYMgBr
(Y = S, Se) was reported [12].
We tried to synthesize organoselenium and organo-
tellurium compounds according to the procedure based
on reaction of elemental chalcogens (activated to
polychalcogenide anions in basic–reductive system
hydrazine hydrate–alkali) with chloromethyl heptyl
ether (I) having a sufficiently long (C7) hydrophobic
residue. Ether I possesses two potential leaving groups
at the electrophilic center (carbon atom). Published
data on reactions of chalcogen-containing anions with
electrophiles containing even two similar leaving
1802

REACTIONS OF CHLOROMETHYL HEPTYL ETHER WITH SELENIUM AND TELLURIUM
1803
Thus the reaction of chloromethyl heptyl ether I
with chalcogenide ions may be expected to occur with
replacement of either one (chlorine atom) or both
nucleofuges.
selane (IV) and 64% of bis(heptyloxymethyl)diselane
(V) (Scheme 3). In this case, products of alkaline hy-
drolysis of ether I were formed in an overall yield not
exceeding 2% (GLC data). We failed to isolate com-
pounds IV and V as individual substances by vacuum
distillation because of their low volatility. They under-
went complete decomposition without going to the gas
phase even under a residual pressure of 1 mm. Their
decomposition was also observed during GLC and
GC–MS analysis. Therefore, compounds IV and V
It is well known that chloromethyl ethers are highly
reactive compounds which can be used in various syn-
theses [13]. In addition, they are important models for
studying theoretical problems of organic chemistry,
e.g., by NQR spectroscopy [14].
1
were identified by H, 13C, and 77Se NMR spectra of
Uehlin and Wirth [15] previously synthesized bis-
(methoxymethyl)diselane in 60–80% yield under
ultrasonic activation from chloromethyl methyl ether
and sodium diselenide prepared from elemental sele-
nium and metallic sodium in THF (in the presence of
naphthalene as catalyst), and the product was success-
fully used to obtain selenium-containing electrophilic
reagents [15].
their mixture.
Scheme 3.
I
+
K2Se2
C7H15OCH2SeCH2OC7H15
IV
+
C7H15OCH2SeSeCH2OC7H15
V
Taking into account that generation of dichalco-
genide ions Y22– (Y = Se, Te) from elemental chalco-
gens in the system hydrazine hydrate–alkali [16] is
more facile from the preparative viewpoint, we
examined reactions of chloromethyl heptyl ether (I)
with selenium and tellurium in that system. Prelim-
inarily, we found that ether I in hydrazine hydrate–
H2O–KOH at 40–45°C in 5 h undergoes complete
conversion (according to the GLC data); from the
reaction mixture we isolated 38% of heptan-1-ol (II)
and 28% of bis(heptyloxy)methane (III) (Scheme 1).
Presumably, formaldehyde acetal III is formed via
well known reaction of alcohols with chloromethyl
ethers [13].
Mixture IV/V was treated with the system hydra-
zine hydrate–KOH, which is known to reduce organic
diselenides at the Se–Se bond [16]. In this process, bis-
(heptyloxymethyl)selane (IV) remained unchanged
and was isolated by treatment of the reaction mixture
with an organic solvent (CH2Cl2). Reductive cleavage
of bis(heptyloxymethyl)diselane (V) produced potas-
sium selenolate VI which was subjected to alkylation
with methyl iodide to obtain 94% of methyl(heptyl-
oxymethyl)selane (VII) (Scheme 4).
Scheme 4.
N2H4 ·H2O–KOH
V
C7H15OCH2SeK
Scheme 1.
VI
H2O, KOH
MeI
–KI
C7H15OCH2Cl
C7H15OH
C7H15OCH2SeMe
VII
–KCl, –H2C=O
I
II
I
Compound VII was isolated as individual sub-
stance and was characterized by spectral data. In
addition, compound VII was synthesized in another
way, from chloromethyl ether I and dimethyldiselane
(Scheme 5).
C7H15OCH2OC7H15
–HCl
III
The reduction of selenium and tellurium in hydra-
zine hydrate–KOH at a chalcogen-to-KOH molar ratio
of 1:1 results mainly in the formation of potassium
dichalcogenides [16] (Scheme 2).
Scheme 5.
2 Me2Se2 + 4 KOH + N2H4 ·H2O
4MeSeK + N2 + 5H2O
Scheme 2.
4 Y + 4 KOH + N2H4 · H2O
2 K2Y2 + N2 + 5 H2O
MeSeK
I
VII
–KCl
The reaction of potassium diselenide thus obtained
with chloromethyl heptyl ether (I) under optimized
conditions afforded 32% of bis(heptyloxymethyl)-
However, the yield of VII according to this scheme
was only 31%, while the major product was heptan-1-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 12 2011

LEVANOVA et al.
1804
ol (II) (yield 50%). Formaldehyde diheptyl acetal (III)
was formed in 10% yield. Dimethyldiselane was
regenerated during the process (52% of the initial
amount). This reaction path is likely to predominate
due to higher basicity of the medium required for the
reductive cleavage of dimethyldiselane (hydrazine
hydrate–KOH without water and excess alkali with
respect to diselane) [16].
0.25 μm; carrier gas helium, flow rate 0.7 ml/min;
injector temperature 250°C, oven temperature pro-
gramming from 60 to 260°C at a rate of 15 deg/min;
detector temperature 250°C, ion source temperature
200°C; quadrupole mass analyzer, electron impact,
70 eV).
Reaction of chloromethyl heptyl ether (I) with
hydrazine hydrate–KOH. Ether I, 6.6 g (40 mmol),
was added at 40–45°C to a solution of 2.1 g (40 mmol)
of potassium hydroxide in a mixture of 1 ml of hydra-
zine hydrate and 2 ml of water. The mixture was
stirred for 5 h (GLC), cooled to 25°C, diluted with
5 ml of water, and treated with 10 ml of methylene
chloride. The extract was dried over MgSO4, and the
solvent was removed. According to the GLC data, the
residue, 4.0 g, contained 1.7 g (38%) of heptan-1-ol
(II) and 1.3 g (28%) of bis(heptyloxy)methane (III).
The reaction of potassium ditelluride K2Te2 with
chloromethyl ether I was also accompanied by forma-
tion of heptan-1-ol (II, 36%) and acetal III (6%).
Organotellurium compounds, bis(heptyloxymethyl)-
tellane (VIII) and bis(heptyloxymethyl)ditellane
(IX) were formed in 15 and 4% yield, respectively
1
(Scheme 6); they were identified only by H NMR.
Immediately after the reaction was complete and the
organic phase was separated, the ratio of VIII and IX
was 4:1; however, elemental tellurium separated from
the mixture on storage, and the product ratio changed
in favor of bis(heptyloxymethyl)tellane (VIII). Ready
transformation IX→VIII is consistent with the known
instability of most organic ditellurides [17].
Heptan-1-ol (II). bp 65–66°C (2 mm). IR spec-
trum, ν, cm–1: 3334, 2957, 2928, 2872, 2857, 2733,
1476, 1435, 1378, 1342, 1301, 1261, 1246, 1180,
1
1058, 1014, 968, 937, 909, 845, 724. H NMR spec-
trum, δ, ppm: 0.86 t (3H, CH3), 1.18–1.29 m (8H,
CH2), 1.51 m (2H, CH2CH2OH), 3.57 t (2H, CH2OH).
13C NMR spectrum, δC, ppm: 13.93 (CH3); 22.49,
25.63, 29.01, 31.72, 32.67 (CH2); 62.68 (CH2OH).
Mass spectrum: m/z 116 [M]+·.
Scheme 6.
K2Te2
I
C7H15OCH2TeCH2OC7H15
–2KCl
VIII
+
C7H15OCH2TeTeCH2OC7H15
Bis(heptyloxy)methane (III). bp 143–146°C
(2 mm). IR spectrum, ν, cm–1: 3072, 2956, 2929, 2872,
2858, 2767, 1467, 1409, 1379, 1340, 1300, 1263,
1249, 1198, 1170, 1116, 1076, 1034, 958, 928, 861,
IX
Thus the system hydrazine hydrate–KOH makes it
possible to obtain selenium derivatives of formalde-
hyde acetals which can be used in the synthesis of
selenium-containing electrophiles. Analogous organo-
tellurium derivatives are formed in a poor yield.
1
780, 724, 686, 652. H NMR spectrum, δ, ppm: 1.28 t
(3H, CH3), 1.60 m (8H, CH2), 1.91 m (2H, CH2CH2O),
3.89 t (2H, CH2O), 5.13 s (2H, OCH2O). 13C NMR
spectrum, δC, ppm: 14.00 (CH3); 22.57, 26.17, 29.09,
29.59, 31.80 (CH2); 68.19 (CH2CH2O), 95.20
(OCH2O). Mass spectrum: m/z 244 [M]+·. Found, %:
C 73.40; H 13.00. C15H32O2. Calculated, %: C 73.77;
H 13.11. M 244.4.
EXPERIMENTAL
The IR spectra were recorded on a Bruker IFS-25
spectrometer from thin films. The H, 13C, and 77Se
1
Reaction of chloromethyl heptyl ether (I) with
potassium diselenide. Chloromethyl heptyl ether (I),
16.4 g (100 mmol), was added at 40–45°C to a solu-
tion of potassium diselenide prepared from 5.6 g
(100 mmol) of potassium hydroxide, 2.5 ml of hydra-
zine hydrate, 5.5 ml of water, and 7.9 g (100 mmol) of
powdered selenium. The mixture was stirred for 5 h at
that temperature, cooled to 25°C, and diluted with
10 ml of water. The lower organic layer (25.5 g) was
separated. According to the NMR data, the product
mixture contained 32% of bis(heptyloxymethyl)selane
(IV) and 64% of bis(heptyloxymethyl)diselane (V).
NMR spectra were measured on a Bruker DPX-400
instrument at 400.13, 100.61, and 76.31 MHz, respec-
tively, using CDCl3 as solvent and tetramethylsilane
(1H, 13C) or Me2Se (77Se) as internal reference. Initial
chloromethyl heptyl ether (I) and reaction products
were analyzed by GLC on an LKhM 80-MD-2 chro-
matograph (2000×3-mm column packed with 5% of
XE-60 on Chromaton N-AW-HMDS; linear oven tem-
perature programming from 30 to 230°C at a rate of
12 deg/min; carrier gas helium). The mass spectra
were obtained on a Shimadzu GCMS-QP5050A instru-
ment (SPB-5 column, 60000×0.25 mm, film thickness
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 12 2011

REACTIONS OF CHLOROMETHYL HEPTYL ETHER WITH SELENIUM AND TELLURIUM
1805
1
Bis(heptyloxymethyl)selane (IV). H NMR spec-
trum, δ, ppm: 0.85 t (3H, CH3), 1.27 m (8H, CH2),
1.55 m (2H, CH2CH2O), 3.46 t (2H, CH2O), 5.03 s
m. Mass spectrum: m/z (80Se) 224 [M]+·. Found, %:
C 48.56; H 8.67; Se 35.00. C9H20OSe. Calculated, %:
C 48.43; H 8.97; Se 35.43. M 223.2.
2
(2H, OCH2Se, satellites with JH–Se = 17.92 Hz).
b. Dimethyldiselane, 2.2 g (12 mmol), was added to
a solution of 3.2 g (58 mmol) of potassium hydroxide
in 14.5 ml of hydrazine hydrate. The mixture was
stirred for 2.5 h at 80–85°C and cooled to 25°C, 2.4 g
(27 mmol) of chloromethyl ether I was added, and the
mixture was stirred for 3.5 h at 40–45°C, cooled to
25°C, diluted with 10 ml of water, and extracted with
15 ml of methylene chloride. The extract was dried
over MgSO4 and evaporated. According to the GLC
data, the residue contained 0.8 g (50% on the initial
ether I) of heptan-1-ol, 1.0 g (31%) of selane VII, and
0.2 g (10%) of diheptyl acetal III. Dimethyldiselane
was identified by GLC (by comparing with an authen-
13C NMR spectrum, δC, ppm: 14.02 (CH3); 22.55,
26.05, 29.02, 29.09, 31.37 (CH2); 67.76 (OCH2Se),
69.59 (CH2CH2O). 77Se NMR spectrum: δSe 266.23 ppm,
m (2JSe–H = 17.54 Hz).
1
Bis(heptyloxymethyl)diselane (V). H NMR spec-
trum, δ, ppm: 0.85 t (3H, CH3), 1.25 m (8H, CH2),
1.56 m (2H, CH2CH2O), 3.52 t (2H, CH2O), 5.32 s
2
13
(2H, OCH2Se, JH–Se = 20.23 Hz). C NMR spectrum,
δC, ppm: 14.02 (CH3); 22.55, 26.11, 29.09, 29.17,
31.74 (CH2)5; 70.07 (CH2O), 75.16 (OCH2Se).
77Se NMR spectrum: δSe 360.93 ppm, m (2JSe–H
=
20.20 Hz); cf. δSe 365.5 ppm for bis(methoxymethyl)-
selane [10]. According to the GLC and GC–MS data,
the organic layer also contained heptan-1-ol (II) and
formaldehyde diheptyl acetal (III) in an overall yield
of ~2% [the yield was estimated by adding 1.0 g
(10.8 mmol) of toluene to the organic phase].
1
2
tic sample) and H NMR (δ 2.54 ppm, JSe–H
=
11.86 Hz). Heptyloxymethyl(methyl)selane (VII) was
isolated and identified as described above.
Reaction of chloromethyl heptyl ether (I) with
potassium ditelluride. Chloromethyl heptyl ether (I),
9.5 g (58 mmol), was added at 25°C to a solution of
potassium ditelluride K2Te2 prepared from 6.4 g
(50 mmol) of powdered tellurium, 2.8 g (50 mmol) of
potassium hydroxide, and 25 ml of hydrazine hydrate,
and the mixture was stirred for 2 h at 35–40°C.
Elemental tellurium separated from the mixture during
the process, and the mixture was filtered (5.4 g of
tellurium, conversion 16%). The organic layer was
separated from the filtrate; it contained (1H NMR)
1.7 g (15%) of bis(heptyloxymethyl)tellane (VIII) and
0.6 g (4%) of bis(heptyloxymethyl)ditellane (IX).
Heptyloxymethyl(methyl)selane (VII). a. Potas-
sium hydroxide, 2.1 g (37 mmol), and hydrazine
hydrate, 35 ml, were added to 2.9 g of a mixture of
selane IV and diselane V (molar ratio 1:2), prepared
1
as described above [according to the H NMR data, it
contained 2.1 g (5 mmol) of diselane V]. The mixture
was stirred for 2.5 h at 80–86°C, cooled to 25°C, and
extracted with 10 ml of methylene chloride. The
extract was washed with 10 ml of water and dried over
MgSO4, and the solvent was removed to obtain 0.8 g
of bis(heptyloxymethyl)selane (IV) whose spectral
parameters were fully identical to those given above.
Found, %: C 57.35; H 10.24; Se 23.12. C16H34O2Se.
Calculated, %: C 56.97; H 10.09; Se 23.44.
1
Bis(heptyloxymethyl)tellane (VIII). H NMR
spectrum, δ, ppm: 0.86 t (3H, CH3), 1.27 m (8H, CH2),
1.56 m (2H, CH2CH2O), 3.51 t (2H, CH2O), 5.46 s
(2H, OCH2Te, 2JH–Te = 36.80 Hz).
The residue was treated with 1.7 g (12 mmol) of
methyl iodide, and the mixture was stirred for 4 h at
25°C and extracted with 10 ml of methylene chloride.
The extract was dried over MgSO4, and the solvent
was removed. Yield of heptyloxymethyl(methyl)selane
(VII) 2.1 g (94%), bp 114–116°C (1.5 mm). IR spec-
trum, ν, cm–1: 2928, 2856, 2741, 1466, 1429, 1378,
1284, 1262, 1220, 1194, 965, 923, 902, 806, 849, 834,
1
Only one H NMR signal was reliably assigned to
2
compound IX, δ, ppm: 5.84 s (2H, OCH2Te, JH–Te
=
38.4 Hz). Signals from protons in the C7H15 group are
likely to coincide with those of bis(heptyloxymethyl)-
tellane (VIII). After separation of the organic layer, the
aqueous hydrazine phase was extracted with methylene
chloride (15 ml), and the extract was dried over
MgSO4 and evaporated. According to the GLC data,
the residue (3.6 g) contained 2.4 g (36%) of heptan-1-
ol and 0.8 g (6%) of formaldehyde acetal III.
1
782, 723, 602, 592. H NMR spectrum, δ, ppm: 0.86 s
(3H, CH3), 1.27 m (8H, CH2), 1.55 m (2H, CH2CH2O),
2.04 s (3H, CH3Se, JH–Se = 9.54 Hz), 3.49 m (2H,
2
2
CH2O), 4.91 s (2H, OCH2Se, JH–Se = 19.07 Hz).
13C NMR spectrum, δC, ppm: 3.28 (CH3Se, JC–Se
=
2
REFERENCES
61.44 Hz), 13.91 (CH3CH2); 22.46, 26.03, 28.93,
29.09, 31.66 (CH2); 69.05 (CH2O), 69.12 (OCH2Se,
2JC–Se = 76.50 Hz). 77Se NMR spectrum: δSe 267.4 ppm,
1. Kishore, K. and Ganesh, K., Adv. Polymer. Sci., 1995,
vol. 121, p. 81; Triapalhi, S.K., Khandewal, B.L., and
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 12 2011

LEVANOVA et al.
1806
Gupta, S.K., Phosphorus, Sulfur Silicon Relat. Elem.,
9. Levanova, E.P., Grabel’nykh, V.A., Kolesnikov, A.V.,
Klyba, L.V., Zhanchipova, E.R., Albanov, A.I., Russav-
skaya, N.V., and Korchevin, N.A., Russ. J. Org. Chem.,
2009, vol. 45, p. 988.
2002, vol. 177, p. 2285; Gusling, H.J., Coord. Chem.
Rev., 1982, vol. 42, p. 133; Sakae, U., Phosphorus, Sulfur
Silicon Relat. Elem., 2005, vol. 180, p. 721.
2. Nogueira, C.W., Zeni, G., and Rocha, J.B.T., Chem. Rev.,
2004, vol. 104, p. 6255; Behne, D., Alber, D., and
Kyriakopoulos, A., ICP Inf. Newsl., 2004, vol. 30, p. 276;
Mugesh, G., du Mont, W.-W., and Sies, H., Chem. Rev.,
2001, vol. 101, p. 2125.
3. Sadekov, I.D. and Minkin, V.I., Usp. Khim., 1995,
vol. 64, p. 527; Zakharov, A.V., Sadekov, I.D., and
Minkin, V.I., Usp. Khim., 2006, vol. 75, p. 234; Sade-
kov, I.D. and Minkin, V.I., Sulfur Rep., 1997, vol. 19,
p. 285; Shimizu, T. and Kamigata, N., Org. Prep. Proced.
Int., 1997, vol. 29, p. 603.
4. Gubin, S.P., Kataeva, N.A., and Khomutov, G.B., Izv.
Ross. Akad. Nauk, Ser. Khim., 2005, no. 4, p. 811.
5. Trofimov, B.A., Sukhomazova, E.N., Levanova, E.P.,
Alekminskaya, O.V., Grabel’nykh, V.A., Myachina, G.F.,
Korzhova, S.A., Deryagina, E.N., and Skotheim, T.A.,
Sulfur Lett., 1999, vol. 23, p. 99.
10. Petrosyan, V.A., Niyazymbetov, M.E., Baryshniko-
va, T.K., and Dorokhov, V.A., Dokl. Akad. Nauk SSSR,
1988, vol. 302, p. 852.
11. Takikawa, Y., Yamaguchi, M., Sasaki, T., Ohnishi, K.,
and Shimada, K., Chem. Lett., 1994, vol. 23, no. 11,
p. 2105.
12. Nedugov, A.N., Pavlova, N.N., and Usmanova, Z.R.,
Zh. Org. Khim., 1994, vol. 30, p. 70.
13. Pokonova, Yu.V., Galoidefiry (Halo Ethers), Moscow:
Khimiya, 1966.
14. Voronkov, M.G., Feshin, V.P., Nikol’skaya, A.N., Niki-
tin, P.A., Levanova, E.P., Berestennikov, N.I., and Vol-
kov, A.N., Dokl. Akad. Nauk SSSR, 1973, vol. 212,
p. 616.
15. Uehlin, L. and Wirth, T., Phosphorus, Sulfur Silicon
Relat. Elem., 2001, vol. 172, p. 189.
16. Deryagina, E.N., Russavskaya, N.V., Papernaya, L.K.,
Levanova, E.P., Sukhomazova, E.N., and Korche-
vin, N.A., Izv. Ross. Akad. Nauk, Ser. Khim., 2005,
no. 11, p. 2395.
6. Deryagina, E.N., Russavskaya, N.V., Alekminskaya, O.V.,
and Grabel’nykh, V.A., Russ. J. Gen. Chem., 2000,
vol. 70, p. 1931.
7. Paetzold, R. and Knaust, D., Z. Chem., 1970, vol. 10,
17. Magnus, P.D., Comprehensive Organic Chemistry,
Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon,
1979, vol. 3. Translated under the title Obshchaya
organicheskaya khimiya, Moscow: Khimiya, 1985,
vol. 6, p. 55.
p. 269.
8. Levanova, E.P., Grabel’nykh, V.A., Russavskaya, N.V.,
Klyba, L.V., Albanov, A.I., and Korchevin, N.A., Russ.
J. Gen. Chem., 2009, vol. 79, p. 2321.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 47 No. 12 2011