Reactions of β,β′-dichlorodiethyl ether with elemental chalcogens and dimethyl dichalcogenides in the system hydrazine hydrate-base

Article abstract of DOI:10.1134/s1070428008010053

β,β′-Dichlorodiethyl ether reacted with elemental selenium or tellurium, as well as with binary chalcogen mixtures (S/Se, S/Te, or Se/Te), activated in the system hydrazine hydrate-base to give oligomeric products containing oxygen and polychalcogenide fr

Full text of DOI:10.1134/s1070428008010053

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2008, Vol. 44, No. 1, pp. 43–51. © Pleiades Publishing, Ltd., 2008.
Original Russian Text © V.Yu. Vshivtsev, E.P. Levanova, V.A. Grabel’nykh, L.V. Klyba, E.R. Zhanchipova, E.N. Sukhomazova, A.A. Tatarinova,
A.I. Albanov, N.V. Russavskaya, N.A. Korchevin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 1, pp. 50–58.
Dedicated to Full Member of the Russian Academy of Sciences
G.A. Tolstikov on his 75th Anniversary
Reactions of β,β′-Dichlorodiethyl Ether
with Elemental Chalcogens and Dimethyl Dichalcogenides
in the System Hydrazine Hydrate–Base
V. Yu. Vshivtsev, E. P. Levanova, V. A. Grabel’nykh, L. V. Klyba, E. R. Zhanchipova,
E. N. Sukhomazova, A. A. Tatarinova, A. I. Albanov, N. V. Russavskaya, 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 June 5, 2007
Abstract—β,β′-Dichlorodiethyl ether reacted with elemental selenium or tellurium, as well as with binary
chalcogen mixtures (S/Se, S/Te, or Se/Te), activated in the system hydrazine hydrate–base to give oligomeric
products containing oxygen and polychalcogenide fragments in the chain. Reductive cleavage of these
oligomers gave rise to 3-oxapentane-1,5-dichalcogenols and their methyl derivatives. The latter were also
synthesized from β,β′-dichlorodiethyl ether and the corresponding dimethyl dichalcogenides in the system
hydrazine hydrate–KOH.
DOI: 10.1134/S1070428008010053
Like other dihalo ethers, β,β′-dichlorodiethyl ether
(I) is an important reagent used in the synthesis of
complex polyfunctional structures [1]. Ready replace-
ment of the chlorine atoms therein by nucleophilic
reagents such as chalcogenide ions opens the way to
chalcogen-containing oligomers. Known analogs of
such oligomers, prepared from other dihalogen deriva-
tives, exhibit valuable electrical and physicochemical
properties [2–4]. Low molecular weight compounds
containing sulfur, selenium, or tellurium atoms in ad-
dition to oxygen are well known to act as donors in
complex formation processes [5, 6]; these compounds
could give rise to polydentate ligands that are linear
hetero analogs of crown ethers [7].
other important sulfur-containing products. The pres-
ent article reports on the results of our study on the
reactions of β,β′-dichlorodiethyl ether with selenium,
tellurium, and dimethyl dichalcogenides, as well as with
two different chalcogens or dichalcogenides simultane-
ously. Elemental selenium was activated in the system
hydrazine hydrate–aqueous alkali, the molar ratio
Se–KOH being 1:1 to ensure predominant generation
of diselenide ions [11] according to Scheme 1.
Scheme 1.
4Se + 4KOH + N2H4 ·H2O
2K2Se2
+ N2 + 5 H2O
In the reaction of compound I with a solution pre-
pared from elemental selenium and hydrazine hydrate–
aqueous alkali we observed formation of black oligo-
mer IIa (Scheme 2). Structurally related oligomer IIb
was synthesized by reaction of β,β′-dichlorodiethyl
ether with selenium in hydrazine hydrate–2-amino-
ethanol (the Se–N2H4·H2O–NH2CH2CH2OH ratio was
the same as in [11], 8:10:1).
The use of reductive systems based on hydrazine
hydrate in the synthesis of organochalcogen com-
pounds [8] ensures facile conversion of elemental
chalcogens into chalcogenide or polychalcogenide ions
which then effectively react with halogen-containing
electrophiles in the same systems. The reaction of
β,β′-dichlorodiethyl ether (I) with elemental sulfur in
the systems hydrazine hydrate–alkali [9] and hydrazine
hydrate–2-aminoethanol [10] resulted in the formation
of a rare type of thiokols soluble in chloroform and
Elemental tellurium can be activated using hy-
drazine hydrate–KOH without additional solvent [8]
43

VSHIVTSEV et al.
44
Scheme 2.
monomeric unit. This may be due to increase in the
reactivity of polychalcogenides Yx2– with rise in x.
When x > 2, almost no side hydrolysis of β,β′-dichloro-
diethyl ether is observed.
Cl
Cl
n
O
I
nK2Se2
–2nKCl
Activation of selenium in the system hydrazine hy-
drate–2-aminoethanol also requires excess compound I
to achieve complete decoloration of the selenium solu-
tion, but the concentration of selenium in oligomer IIb
thus formed is even smaller than the theoretical value.
A probable reason is the presence in the system of
a large excess of hydrazine; being an effective reduc-
ing agent, it hampers increase of x.
Se
Se
O
n
IIa
n = 7, 8.*
(Scheme 3). The reaction of I with a solution of potas-
sium ditelluride thus obtained gave 87% of oligomeric
product III (Scheme 4)
In the reactions with two different chalcogens, each
of them was activated separately according to Schemes
1 and 3, and the resulting chalcogen solutions were
combined and brought into reaction with compound I
(Scheme 5).
Scheme 3.
2x Te + 4 KOH
+ N2H4 ·H2O
2 K2Tex
+
N2
O
+ 5 H2O
Scheme 4.
Scheme 5.
nK2Te2
–2nKCl
Te
Tex–1
0.5n K2Y2 + 0.5nK2Y2'
nI
Y
Y'
nI
O
n
–2nKCl
n
III
IV–VI
n = 28.*
IV, Y = S, Y′ = Se; V, Y = S, Y′ = Te; VI, Y = Se, Y′ = Te.
The products, oligomeric compounds IV–VI were
enriched in the heavier chalcogen; correspondingly,
the concentration of the lighter chalcogen therein was
underestimated. In these reactions, apart from hydrol-
ysis of I, an additional interaction between chalco-
genide ions is possible due to their different abilities to
undergo redox reactions [12]. Such a behavior of chal-
cogenides, especially of tellurides, in hydrazine hy-
drate-based systems was reported by us previously
[13] (Scheme 6).
The properties of oligomers IIa, IIb, and III are
given in Experimental. In all cases, the amount of di-
chlorodiethyl ether I was larger than its stoichiometric
amount according to Scheme 2 or 4 (Y:I = 2:1) in
order to achieve complete decoloration of selenium
and tellurium solutions. Nevertheless, the concentra-
tion of selenium and tellurium in the resulting oligo-
mers IIa and III, respectively, considerably exceeded
the theoretical value. Obviously, chloro ether I in the
system hydrazine hydrate–KOH undergoes partial
alkaline hydrolysis to give diethylene glycol or poly-
ethylene glycols that are readily soluble in aqueous
hydrazine. In keeping with the data of [8], alkaline
hydrolysis of other halogen derivatives almost did not
occur in analogous systems. Side hydrolysis processes
reduce the overall basicity of the system, which favors
increased number of chalcogen atoms (x) in polychal-
cogenide ions Yx2–. However, in the reaction of I with
K2Te2.5 prepared according to Scheme 3 (KOH–Te
ratio 2:2.5) only stoichiometric amount of the former
was necessary to complete the process (decoloration of
the polytelluride solution). The concentration of tellu-
rium in the resulting oligomer IIIa was similar to the
calculated value for (TeCH2CH2OCH2CH2Te1.5) as
Scheme 6.
Te22–
+
Y22–
+
2Te
+
2Y22–
Te22–
Te
Te23–
Y = S, Se.
Among compounds II–VI, only IIb is soluble in
chloroform (and CDCl3), so that we were able to
record its 1H NMR spectrum (see Experimental) which
indicated fairly uniform distribution of selenium atoms
over polyselenide fragments in the oligomer (Se2).
Taking into account the concentration of residual chlo-
rine, we calculated the molecular weight of oligomer
IIb and determined its average molecular formula:
* The n value was estimated from the concentration of residual
chlorine atoms at the ends of macromolecules.
Cl(CH2)2O(CH2)2Se[Se(CH2)2O(CH2)2Se]9Se(CH2)2O(CH2)2Cl.
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REACTIONS OF β,β′-DICHLORODIETHYL ETHER WITH ELEMENTAL CHALCOGENS
45
Despite relatively low average molecular weight,
oligomers IIa and IV are soluble only partially, and the
insoluble part is characterized by a larger average mo-
lecular weight (3200 a.m.u. for the insoluble fraction
of IIa); obviously, oligomers with a lower molecular
weight are soluble better, and the polyselenide frag-
ments therein are shorter.
undergo reductive cleavage at the Y–Y bond to give
the corresponding bis-chalcogenolates IX. Oligomers
II and III having similar chalcogen atoms give rise to
symmetric bis-chalcogenolates IXa–IXc (Scheme 9),
while those containing different chalcogen atoms
(IV–VI) are converted into both symmetric derivatives
IXa–IXc and bis-chalcogenolates IXd–IXf with dif-
ferent chalcogen atoms (Scheme 10).
After separation of oligomers from the reaction
mixture, the aqueous hydrazine layer was extracted
with methylene chloride to isolate two types of hetero-
cyclic compounds, 1,4-oxachalcogenanes VIIa–VIIc
and 1-oxa-4,5-dichalcogenepanes VIII (Schemes 7
and 8). Among the latter, only derivatives VIIIa–VIIIc
having similar chalcogen atoms and 1,4,5-oxathiase-
lenepane (VIIId) were identified by gas chromatog-
raphy–mass spectrometry. The yield of compounds VII
was as low as 5–10%; however, these heterocycles are
important from the viewpoint of both theoretical and
applied organic chemistry [14]. With selenium-con-
taining derivative VIIb as an example we showed that
they can be obtained in 45% yield using dilute solu-
tions of chalcogens activated via conversion into chal-
cogenide ions (K2Y). Compounds VII and VIII are
likely to be formed concurrently with the formation of
oligomers.
Scheme 9.
N2H4 ·H2O, KOH
KY
YK
II or III
O
IXa–IXc
Y = S (a), Se (b), Te (c).
Scheme 10.
N2H4 ·H2O, KOH
IV–VI
IXa–IXc
Y'K
KY
+
O
IXd–IXf
Y = S, Y′ = Se (d), Te (e); Y = Se, Y′ = Te (f).
Treatment of bis-selenolate IXb with an acid under
mild conditions (0°C, argon) gave 8% of very unstable
3-oxapentane-1,5-diselenol (X) (Scheme 11). Its high
reactivity follows from the formation of a large amount
(45%) of the corresponding oxidation product, 1,4,5-
oxadiselenepane (VIIIb) during the process. The struc-
ture of X was confirmed by the IR (νSeH 2295 cm–1),
1H and 13C NMR (see Experimental), and GC–MS data
(the mass spectrum contained peaks from fragment
ions having a SeH moiety; no such peaks were present
in the mass spectrum of VIIIb). Selenium analogs of
thiols remain so far rare and difficultly accessible
compounds [15]; therefore, the above reaction attracts
practical interest despite poor yield of X.
Scheme 7.
Y
I
+
K2Y
–2KCl
O
VIIa–VIIc
Y = S (a), Se (b), Te (c).
Scheme 8.
Y
I
+
K2YY'
Y'
–2KCl
O
VIIIa–VIIIc
Scheme 11.
Y = Y′ = S (a), Se (b), Te (c); Y = S, Y′ = Se (d), Te (e).
HCl
HSe
SeH
IXb
O
–KCl
1
13
The H and C NMR and mass spectra of 1,4-oxa-
chalcogenanes VIIa–VIIc are given in Experimental.
The mass spectra of the selenium- and tellurium-con-
taining compounds are similar, while 1,4-oxathiane
(VIIa) is characterized by somewhat different mass
spectrum due to considerable contribution of frag-
mentation pathway involving elimination of CH2O
molecule.
X
O2 –H2O
HCl, O2
–KCl, –H2O
VIIIb
Our attempt to obtain 3-oxapentane-1,5-ditellurol
(Xa) under analogous conditions resulted in the forma-
tion of a black material which contained 1,4,5-oxadi-
tellurepane (VIIIc) (no more than 10%, according to
Like other oligomeric dichalcogenides [8, 13] com-
pounds II–VI in the system hydrazine hydrate–alkali
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 1 2008

VSHIVTSEV et al.
46
1
Scheme 14.
the H NMR data) and other compounds. Insofar as
reliable published data on spectral parameters of tel-
lurols are lacking, it is difficult to assert with certainty
that compound Xa is present or absent in the reaction
mixture. Nevertheless, treatment of the product mix-
ture with hydrazine hydrate–KOH and subsequent addi-
tion of methyl iodide to the homogeneous solution thus
formed gave 75% of 5-oxa-2,8-ditelluranonane (XIc).
N2H4 ·H2O, KOH
Me2Y2
2MeYK
MeYK, MeY'K
–2KCl
I
XIa–XIc + XId–XIf
Y = S, Se, Te.
methyl disulfide and dimethyl diselenide, the alkyla-
tion at 40–45°C in 1 h gave a considerable amount of
intermediate products XIIa and XIIb (Scheme 15).
Bis-chalcogenolates IX formed as a result of reduc-
tive cleavage of oligomers II–VI (Schemes 9, 10) were
subjected (without isolation) to alkylation with methyl
iodide. We thus obtained symmetric (XIa–XIc) and
unsymmetric (XId–XIf) methyl derivatives of the cor-
responding 1,5-dichalcogenols (Scheme 12).
Scheme 15.
MeS
Cl
2 I + MeSK + MeSeK
O
XIIa
MeSe
Cl
+
Scheme 12.
O
2MeI
Y3Me
Y3Me
XIIb
MeSeK
IXa–IXf
O
–2KCl
XIIa or XIIb + MeSK
+
XIa, XIb, XId
XIa–XIc
Y1Me
Y2Me
Raising the temperature led to complete conversion
of XII into XI. However, even under these conditions,
traces of MeTeCH2CH2OCH2CH2Cl (XIIc) were
formed from a mixture of Me2S2 with Me2Te2 or of
Me2Se2 with Me2Te2. Compounds XIIa–XIIc were
identified by GC–MS. Among cyclic by-products, only
1,4-oxatellurane (VIIc) was detected. The formation of
the latter indicates that dimethyl ditelluride is unstable
and that its reductive cleavage may be accompanied by
decomposition with liberation of elemental tellurium,
which is typical of many organic ditellurides [16]. The
subsequent activation of tellurium via conversion into
K2Te enables the reaction with compound I according
to Scheme 7.
+
O
XId–XIf
Y3 = S (a), Se (b), Te (c); Y1 = S, Y2 = Se (d), Te (e);
Y1 = Se, Y2 = Te (f).
The yields of 5-oxa-2,8-dichalcogenanonanes XIa–
XIf and by-products, their physical constants, and spec-
tral parameters are given in Experimental. 1,4,5-Oxa-
dichalcogenepanes VIII in the system hydrazine
hydrate–KOH also undergo reductive cleavage with
formation of dichalcogenolates IX. For example,
1,4,5-oxadiselenepane (VIIIb) obtained according to
Scheme 11 was converted into 6-oxa-3,9-diselenaun-
decane (XIg) in 74% yield (Scheme 13).
Thus we have developed synthetic approaches to
oligomeric, linear, and cyclic compounds having con-
formationally labile C–O bonds and heavy chalcogen
atoms using accessible reagents. The proposed proce-
dures are convenient from the preparative viewpoint.
Scheme 13.
N2H4 ·H2O, KOH
VIIIb
2EtBr
–2KBr
IXb
EtSe
SeEt
O
EXPERIMENTAL
XIg
The IR spectra were measured on a Specord 75IR
spectrometer from samples prepared as thin films and
on a Bruker IFS-25 instrument from samples pelleted
Compounds XI are stable multidentate ligands con-
taining two chalcogen atoms in addition to oxygen
atom. Taking into account their possible application in
complex formation processes [7], we have developed
another synthetic approach to these compounds on the
basis of reductive cleavage of dimethyl dichalco-
genides, followed by alkylation of methanechalco-
genolates with β,β′-dichlorodiethyl ether (I), as shown
in Scheme 14. In the reaction with a mixture of di-
with KBr. The H, 13C, Se, and 125Te NMR spectra
were recorded on a Bruker DPX-400 spectrometer at
400.13, 100.62, 76.3, and 126.2 MHz, respectively,
using CDCl3 as solvent and HMDS as internal refer-
ence. The mass spectra were obtained on a Shimadzu
GCMS-QP5050A instrument (SPBTM-5 capillary col-
umn, 60000×0.25 mm, film thickness 0.25 μm; injec-
1
77
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REACTIONS OF β,β′-DICHLORODIETHYL ETHER WITH ELEMENTAL CHALCOGENS
47
tor temperature 250°C; carrier gas helium, flow rate
0.7 ml/min; oven temperature programming from 60 to
260°C at a rate of 15 deg/min; detector temperature
250°C; quadrupole mass analyzer; electron impact
ionization, 70 eV; ion source temperature 200°C;
a.m.u. range 34–650). Liquid products were analyzed
by GLC on LKhM 80-MD-2 (2000×3-mm column,
stationary phase 5% of DC-550 on Chromaton N-AW-
HMDS; linear oven temperature programming at a rate
of 12 deg/min; carrier gas helium) and Tsvet-500
chromatographs (2000×5-mm steel column, stationary
phase 5% of XE-60 on Chromaton N-AW-HMDS;
linear oven temperature programming from 30 to
230°C at a rate of 12 deg/min; carrier gas helium).
(CH2O). Mass spectrum, m/z (I/Itot, %): 232 (17.3)
[M]+·, 204 (2.5) [M – C2H4]+·, 160 (29) [SeSe]+·, 43
(23) [C3H7]+, 41 (1) [C3H5]+.
The reaction of 3.65 g (0.025 mol) of compound
I with a solution of K2Se prepared from 3.28 g
(0.058 mol) of KOH, 9 g of (0.18 mol) of hydrazine
hydrate, 90 ml of water, and 2 g (0.025 mol) of
powdered selenium (Se–KOH molar ratio 1:2.3) under
analogous conditions gave a mixture containing (ac-
cording to the GLC data) 1,4-oxaselenane (VIIb, 45%,
calculated on the initial compound I) and 1,4,5-oxadi-
selenepane (VIIIb, 10%).
Oligomer IIb. A flask was charged with 7.5 g
(0.15 mol) of hydrazine hydrate, 0.95 g (0.015 mol) of
2-aminoethanol, and 4 g (0.05 mol) of powdered sele-
nium. The mixture was heated for 2 h at 70–75°C and
cooled to 50°C, 5.4 g (0.038 mol) of compound I was
added (Se–I molar ratio 1.3:1), and the mixture was
stirred for 3.5 h at 60–70°C. Yield 4.2 g (72%, cal-
culated on the initial selenium), mp 86–140°C
(decomp.), M 2200. IR spectrum, ν, cm–1: 2926, 2851,
2779, 2725 w, 1470, 1440, 1414, 1395, 1351, 1272,
1180, 1102 v.s, 1031, 982, 931, 745, 667, 550 v.w.
1H NMR spectrum, δ, ppm: 2.75 m (2H, CH2Se),
3.11 m (2H, CH2Se2), 3.28 m (2H, CH2Se3), 3.35 m
(2H, CH2Se4) (intensity ratio 1:40:8:1), 3.76 m (2H,
CH2O), 3.83 m (2H, CH2Cl). Found, %: Cl 3.21;
Se 65.31. Calculated, %: Se 68.70. The aqueous
hydrazine phase was extracted with chloroform, and
the extract contained 10% of 1,4-oxaselenane (VIIb)
and 2% of 1,4,5-oxadiselenepane (VIIIb). Removal of
the solvent from the extract gave almost pure com-
pound VIIb.
Oligomer IIa. A mixture of 2.8 g (0.05 mol) of
potassium hydroxide, 2.5 g (0.05 mol) of hydrazine
hydrate, 15 ml of water, and 3.95 g (0.05 mol) of
powdered selenium was heated for 2 h at 80–85°C and
cooled to room temperature, and 4.18 g (0.029 mol) of
β,β′-dichlorodiethyl ether (I) was added (Se–I molar
ratio 1.7:1). The mixture was stirred for 2 h at 65–
70°C, and the precipitate of IIa was separated, washed
with water, and dried. Yield 4.33 g (75%, calculated
on the initial selenium), mp 86–140°C (decomp.),
M 1750. IR spectrum, ν, cm–1: 2925, 2851, 2782 w,
1467, 1413, 1352, 1272, 1180, 1102 v.s, 1031, 983,
932 w, 746, 668. Found, %: Cl 4.10; Se 74.93. Cal-
culated, %: Se 68.70 (per monomeric unit). Treatment
of oligomer IIa with chloroform gave a dark brown
extract and a black insoluble residue (found, %:
1
Se 93.73; Cl 2.25). The H NMR spectrum of the
chloroform solution contained the following signals, δ,
ppm: 2.76 m (CH2Se), 3.11 m (CH2Se2), 3.27 m
(CH2Se3) (intensity ratio 1:25:10). After separation of
oligomer IIa, the aqueous hydrazine layer was treated
with 50 ml of methylene chloride containing 1 g of
toluene. The extract contained 1,4-oxaselenane (VIIb,
5 wt % with respect to the amount of toluene) and
1,4,5-oxadiselenepane (VIIIb, 9%).
Oligomer III. A flask was charged with 2.8 g
(0.05 mol) of potassium hydroxide, 20 g (0.4 mol) of
hydrazine hydrate, and 6.38 g (0.05 mol) of powdered
tellurium. The mixture was heated for 2 h at 85–90°C
and cooled to 50°C, and 4.88 g (0.033 mol) of com-
pound I was added (Te–I molar ratio 1.5 :1). Yield
7.1 g (87%), mp 68–123°C (decomp.), M 9300. IR
spectrum, ν, cm–1: 2968, 2922, 2848, 1471, 1457,
1397, 1346, 1259, 1172, 1070 s, 1049, 1025, 957,
717, 625. Found, %: Cl 0.75; Te 80.20. Calculated, %:
Te 78.05. The aqueous hydrazine phase was extracted
with diethyl ether. The ether extract contained 6% of
1,4-oxatellurane (VIIc) and 3% of 1,4,5-oxaditellure-
pane (VIIIc).
1
Compound VIIb. H NMR spectrum, δ, ppm:
2.65 m (2H, CH2Se), 4.00 m (2H, CH2O). 13C NMR
1
spectrum, δC, ppm: 17.07 (CH2Se, JC, Se = 56 Hz),
77
69.39 (CH2O). Se NMR spectrum: δSe 150.75 ppm.
80
Mass spectrum, m/z (hereinafter, for Se) (I/Itot, %):
152 (16.1) [M]+·, 124 (3.2) [M – C2H4]+·, 108, 107
(33.3) [C2H4Se]+·, [C2H3Se]+, 94 (34.1) [CH2Se]+·, 80
(7.1) [Se]+, 43 (31) [C3H7]+, 41 (33) [C3H5]+.
Compound VIIIb. H NMR spectrum, δ, ppm:
Compound VIIc. 1H NMR spectrum, δ, ppm: 2.76 t
1
13
3.14 t (2H, CH2Se), 3.78 t (2H, CH2O). 13C NMR spec-
(2H, CH2Te), 4.12 t (2H, CH2O). C NMR spectrum,
trum, δC, ppm: 29.29 (CH2Se, JC,Se = 74.5 Hz), 70.75
δC, ppm: –6.42 (CH2Te, 1JC,Te = 134 Hz), 70.95 (CH2O).
1
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 1 2008

VSHIVTSEV et al.
48
125Te NMR spectrum: δTe 177.52 ppm. Mass spectrum,
m/z (hereinafter for 130Te) (I/Itot, %): 202 (19.2) [M]+·,
174 (10.8) [M – C2H4]+·, 158, 157 (14.6) [C2H4Te]+·,
[C2H3Te]+, 144 (13.7) [CH2Te]+·, 130 (22.5) [Te]+, 43
(14.6) [C3H7]+, 41 (2) [C3H5]+.
powdered sulfur; a solution of potassium ditelluride
was prepared using the same amounts of potassium
hydroxide and hydrazine hydrate and 6.4 g (0.05 mol)
of powdered tellurium. The solutions were combined,
the mixture was heated to 50°C, and 8.37 g (0.059 mol)
of compound I was added [(S + Te)–I molar ratio
1.7 :1]. We isolated 4.5 g (39%, calculated on the
initial tellurium) of oligomer V, mp 105–120°C (de-
comp.), M 6900. IR spectrum, ν, cm–1: 2961, 2923,
2850, 1498 v.w, 1475, 1462, 1425, 1406 v.w, 1377,
1347, 1271, 1177, 1141, 1091 v.s, 1073, 1027, 955,
888, 716, 436 w, 418. Found, %: Cl 1.02; S 1.25;
Te 80.54. Calculated, %: C 13.79; Te 55.17. The aque-
ous hydrazine phase was extracted with methylene
chloride. The extract contained 7% of oxathiane VIIa,
4% of oxatellurane VIIc, and traces of 1,4,5-oxathia-
tellurepane (VIIIe).
Compound VIIIc. Mass spectrum, m/z (I/Itot, %):
332 (23.6) [M]+·, 304 (5.8) [M – C2H4]+·, 260 (39.3)
[TeTe]+·, 43 (10) [C3H7]+, 41 (3) [C3H5]+.
The reaction of 1.8 g (0.0125 mol) of compound I
with a solution prepared from 3.95 g (0.03 mol) of
tellurium, 1.4 g (0.025 mol) of potassium hydroxide
(Te–KOH molar ratio 2.5:2.0), and 10 g (0.2 mol) of
hydrazine hydrate under the conditions described
above for the synthesis of oligomer III (Te–I molar
ratio 2:1) gave 3.2 g (65%, calculated on the initial
tellurium) of oligomer IIIa, mp 70–130°C (decomp.),
M 2450. IR spectrum, ν, cm–1: 2930, 2851, 1463, 1450,
1425, 1406, 1390, 1346, 1296, 1279, 1258, 1175, 1140,
1091, 1071, 1027, 958, 711, 444. Found, %: Cl 2.81;
Te 82.00. Calculated, %: Te 82.00.
A solution of potassium diselenide was prepared
from 2.8 g (0.05 mol) of potassium hydroxide, 20 g
(0.4 mol) of hydrazine hydrate, and 4 g (0.05 mol) of
powdered selenium; a solution of potassium ditelluride
was prepared using the same amounts of potassium
hydroxide and hydrazine hydrate and 6.4 g (0.05 mol)
of powdered tellurium. The solutions were combined,
the mixture was heated to 50°C, and 10.8 g (0.076 mol)
of compound I was added [(Se+Te)–I molar ratio
1.4:1]. We isolated 7 g (50%, calculated on the initial
tellurium) of oligomer VI, mp 100–115°C (decomp.).
IR spectrum, ν, cm–1: 2958 w, 2920, 2850, 1464, 1403,
1348, 1261, 1160, 1094 v.s, 1075, 1026, 978, 668 w,
502. Found, %: Se 14.96; Te 67.30. Calculated, %:
Se 28.32; Te 45.88. The aqueous hydrazine phase was
extracted with methylene chloride. The extract con-
tained 7% of 1,4-oxaselenane (VIIb) and 4% of
1,4-oxatellurane (VIIc).
Oligomers IV–VI (general procedure). A solution
of potassium disulfide was prepared from 1.4 g
(0.025 mol) of KOH, 1.25 g (0.025 mol) of hydrazine
hydrate, 7.5 ml of water, and 0.8 g (0.025 mol) of
powdered sulfur. A solution of potassium diselenide
was prepared using the same amounts of KOH,
hydrazine hydrate, and water and 2 g (0.025 mol) of
powdered selenium. The solutions were combined, the
mixture was heated to 50°C, and 3.9 g (0.027 mol) of
compound I was added [(S+Se)–I molar ratio 2:1].
We isolated 2.4 g (51%, calculated on the initial
selenium) of oligomer IV, mp 118–130°C (decomp.),
M 1790. IR spectrum, ν, cm–1: 3483 w, 2919, 2854 s,
2783, 2727 w, 1470, 1450, 1415, 1398, 1353, 1275 s,
1182, 1104 v.s, 1033, 984, 745, 667, 486. Found, %:
Cl 3.97; S 16.02; Se 59.21. Calculated, %: C 17.49;
Se 43.16. The aqueous hydrazine layer was extracted
with methylene chloride. The extract contained 7% of
1,4-oxathiane (VIIa), 6% of 1,4-oxaselenane (VIIb),
3% of 1,4,5-oxadiselenepane (VIIIb), and 2% of 1,4,5-
oxathiaselenepane (VIIId). 1H NMR spectrum of VIIa,
δ, ppm: 2.58 t (2H, CH2S), 3.75 t (2H, CH2O).
13C NMR spectrum, δC, ppm: 27.00 (CH2S), 68.62
(CH2O). Mass spectrum of VIIId, m/z (I/Itot, %): 184
(11.8) [M]+·, 140 (11.1) [M – C2H4O]+·, 112 (14.3)
[SSe]+·, 61 (4.5) [C2H5S]+, 43 (20) [C3H7]+, 41 (1)
[C3H5]+.
3-Oxapentane-1,5-diselenol (X). Oligomer IIa,
5 g (0.022 mol), was dissolved in a mixture of 15 g
(0.3 mol) of hydrazine hydrate and 5 g (0.089 mol) of
potassium hydroxide on heating for 2.5 h at 75–80°C.
The mixture was cooled to 25°C and poured into
a mixture of ice with 40 ml of concentrated hydro-
chloric acid under stirring in a stream of argon. An oily
material separated and was extracted into methylene
chloride. The extract was purged with argon and dried
over MgSO4. The solvent was distilled off, and the
residue (2.66 g, a mixture of compounds X and VIIIb)
was subjected to vacuum distillation. A fraction with
bp 105°C (2 mm) was almost pure diselenol X. Yield
0.41 g (8%), light yellow oily substance. 1H NMR spec-
A solution of potassium disulfide was prepared
from 2.8 g (0.05 mol) of potassium hydroxide, 20 g
(0.4 mol) of hydrazine hydrate, and 1.6 g (0.05 mol) of
1
trum, δ, ppm: –0.46 t (1H, SeH, JSe, H = 46.7 Hz),
2.74 m (2H, CH2Se), 3.66 t (2H, OCH2). 13C NMR
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 44 No. 1 2008

REACTIONS OF β,β′-DICHLORODIETHYL ETHER WITH ELEMENTAL CHALCOGENS
49
spectrum, δC, ppm: 16.76 (CH2Se, JC,Se = 51.2 Hz),
72.35 (CH2O). Mass spectrum, m/z (I/Itot, %): 109 and
108 (23) [C2H4SeH]+, 95 and 93 (18) [CH2SeN]+,
[CHSe]+, 81 and 80 (24) [HSe]+, [Se]+. Found, %:
C 20.78; H 4.18; Se 67.42. C4H10OSe2. Calculated, %:
C 20.69; H 4.31; Se 68.09.
isolated 52% of 5-oxa-2,8-diselenanonane (XIb),
1
bp 98–100°C (2 mm). H NMR spectrum, δ, ppm:
2
2.02 s (3H, CH3Se, JH, Se = 10.3 Hz), 2.70 t (2H,
CH2Se), 3.69 t (2H, CH2O). 13C NMR spectrum, δC,
2
ppm: 4.51 (CH3Se, JC, Se = 62 Hz), 24.19 (CH2Se,
2JC,Se = 63 Hz), 70.80 (OCH2). Mass spectrum, m/z
(I/Itot, %): 262 (8.9) [M]+·, 247 (8.2) [M – CH3]+, 203
(2.5), 175 (3.6), 123 (19.4), 108 (8.3), 95 (16.5), 41
(1.9). Found, %: C 27.77; H 5.38; Se 60.99. C6H14OSe2.
Calculated, %: C 27.70; H 5.39; Se 60.76.
1,4,5-Oxadiselenepane (VIIIb) was the main com-
ponent of a fraction with bp 125–130°C (2 mm). Yield
2.24 g (45%), yellow oily substance. No absorption
band at 2295 cm–1 (νSe–H) was present in the IR spec-
trum. Found, %: C 21.61; H 3.69; Se 67.68. C4H8OSe2.
Calculated, %: C 20.87; H 3.48; Se 68.68.
From oligomer IIb we obtained 79% of compound
XIb. Oligomer III gave rise to 65% of 5-oxa-2,8-di-
telluranonane (XIc), bp 137–140°C (2 mm) and 20%
of 1,4-oxatellurane (VIIc), bp 58–62°C (2 mm).
Reductive cleavage of oligomer III. Compound
III, 5.6 g (0.017 mol), was dissolved at 80–85°C in
a mixture of 4.9 g (0.087 mol) of potassium hydroxide
and 15 g (0.3 mol) of hydrazine hydrate. The mixture
was poured into a mixture of 110 g of ice and 92 ml of
concentrated hydrochloric acid in a stream of argon.
Abundant precipitation of elemental tellurium and gas
evolution were observed. The mixture was extracted
with methylene chloride, the extract was filtered from
tellurium and dried over MgSO4, and the solvent was
distilled off under reduced pressure. The residue, 2.4 g,
was a dark red liquid. According to the GC–MS data,
it contained 1,4-oxatellurane (VIIc) and unidentified
products. IR spectrum, ν, cm–1: 3451, 3041, 2972,
2927, 2851, 2770, 2715 v.w, 2299 v.w, 2125 v.w,
2027 w, 1621, 1468, 1450, 1404, 1380, 1346, 1263,
1195, 1173, 1141, 1093, 1073, 1027, 991 w, 955, 907,
889, 735, 701, 627, 537, 499, 477. 1H NMR spectrum,
δ, ppm: 2.80 m, 3.32 m, 3.72 m (intensity ratio 2:3:5).
1
Compound XIc. H NMR spectrum, δ, ppm: 1.90 s
2
(3H, CH3Te, JH, Te = 20.3 Hz), 2.76 t (2H, CH2Te),
3.72 t (2H, OCH2). 13C NMR spectrum, δC, ppm:
–22.19 (CH3Te, 1JC,Te = 158 Hz), 2.44 (CH2Te, 1JC,Te
=
159.3 Hz), 72.04 (OCH2). 125Te NMR spectrum:
δTe 184.33 ppm. Mass spectrum, m/z (I/Itot, %): 362
(4.5) [M]+·, 347 (16.5), 275 (11.9), 173 (5.3), 145
(27.3), 130 (9.2), 43 (4.1), 41 (1.0). Found, %: C 20.91;
H 4.06; Te 70.68. C6H14OTe2. Calculated, %: C 20.16;
H 3.92; Te 71.44.
From oligomer IV we obtained 4% of 5-oxa-2,8-
dithianonane (XIa), bp 92–96°C (2 mm), 8% of 5-oxa-
2,8-diselenanonane (XIb), 5% of 5-oxa-2-thia-8-
selenanonane (XId), bp 96°C (2 mm), 2% of 1,4-oxa-
thiane (VIIa), and 1% of 1,4-oxaselenane (VIIb).
1
Compound XIa. H NMR spectrum, δ, ppm: 2.14 s
1
(3H, CH3S), 2.67 t (2H, CH2S), 3.62 t (2H, CH2O).
13C NMR spectrum, δ, ppm: 15.88 (CH3S), 33.37
(CH2S), 70.11 (OCH2). Mass spectrum, m/z (I/Itot, %):
166 w [M]+·, 75 (24.7), 74 (27.7), 61 (6.4), 47 (11.5),
41 (14.0). Found, %: C 43.00; H 8.20; S 38.00.
C6H14OS2. Calculated, %: C 43.40; H 8.40; S 38.55.
According to the H NMR data, the residue contained
10% of 1,4-oxatellurane (VIIc).
A 0.93-g portion of the residue was dissolved in
a mixture of 1 g (0.018 mol) of potassium hydroxide
and 3.75 g (0.075 mol) of hydrazine hydrate on heating
to 80–85°C, and a required amount of methyl iodide
was added dropwise to the resulting solution. The mix-
ture was extracted with methylene chloride, the solvent
was distilled off, and the residue was evacuated to
obtain 0.75 g of a product which was identified as
5-oxa-2,8-ditelluranonane (XIc) on the basis of the
GC–MS and 1H NMR data (see below).
Compound XId. 1H NMR spectrum, δ, ppm: 2.02 s
2
(3H, CH3Se, JH, Se = 10.5 Hz), 2.14 s (3H, CH3S),
2.68 t (2H, CH2Se), 3.64 t (2H, OCH2CS), 3.69 t (2H,
OCH2CSe). 13C NMR spectrum, δC, ppm: 4.54 (CH3Se,
2JC,Se = 61 Hz). Mass spectrum, m/z (I/Itot, %): 214
(4.3) [M]+·, 139 (4.3), 123 (7.4), 95 (9.7), 75 (3.4), 61
(5.8), 47 (6.9), 41 (22.6). Found, %: C 34.81; H 6.60;
S 14.73; Se 36.13. C6H14OSSe. Calculated, %: C 33.81;
H 6.57; S 15.03; Se 37.08.
5-Oxa-2,8-dichalcogenanonanes XIa–XIf (gen-
eral procedure). a. Oligomer II–VI was dissolved in
the system hydrazine hydrate–potassium hydroxide, as
described above for compound IIa, and a required
amount of methyl iodide was added dropwise to the
resulting solution at room temperature. The organic
phase was separated, analyzed by GC–MS, and sub-
jected to vacuum distillation. From oligomer IIa we
From oligomer V we obtained 65% of 5-oxa-2,8-
ditelluranonane (XIc), 4% of 5-oxa-2-thia-8-tellura-
nonane (XIe), bp 102–108°C (1.5 mm), and 14% of
1,4-oxatellurane (VIIc). No 5-oxa-2,8-dithianonane
(XIa) was detected among the products.
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VSHIVTSEV et al.
50
1
Compound XIe. H NMR spectrum, δ, ppm: 1.19 s
From a mixture of dimethyl disulfide and dimethyl
ditelluride we obtained 55% of 5-oxa-2,8-dithianonane
(XIa), 25% of 5-oxa-2,8-ditelluranonane (XIc), 58%
of 5-oxa-2-thia-8-telluranonane (XIf), 8% of 1,4-oxa-
tellurane (VIIc), and traces of 1-chloro-3-oxa-6-tel-
luraheptane (XIIc). Mass spectrum of XIIc, m/z (35Cl):
252 [M]+·, 224 [M – C2H4]+, 173 [CH3TeCH2CH2]+,
159 [CH3TeCH2]+, 145 [CH3Te]+, 130 [Te]+, 107 [M –
CH3Te]+, 93 [M – CH3TeCH2]+, 63 [CH2CH2Cl]+, 45
[C2H4OH]+.
(3H, CH3Te, 2JH,Te = 21 Hz), 2.14 s (3H, CH3S), 2.67 t
(2H, CH2Te), 2.78 t (2H, CH2S), 3.62 t (2H, CH2O),
3.75 t (2H, CH2O). 13C NMR spectrum, δC, ppm:
–22.21 (CH3Te, JC,Te = 155 Hz), 16.17 (CH3S), 33.71
(CH2S), 70.21 (OCH2CTe, JC, Te = 160 Hz), 72.13
(OCH2CS). Mass spectrum, m/z (I/Itot, %): 264 (9.1)
[M]+·, 249 (6.2), 145 (13.4), 119 (4.1), 75 (20.9), 61
(7.7), 47 (10.7), 41 (13.5). Found, %: C 27.85; H 5.33;
S 11.61; Te 48.06. C6H14OSTe. Calculated, %: C 27.52;
H 5.35; S 12.23; Te 48.78.
1
1
From a mixture of dimethyl diselenide and dimeth-
yl ditelluride we obtained 79% of 5-oxa-2,8-diselena-
nonane (XIb), 13% of 5-oxa-2,8-ditelluranonane
(XIc), 72% of 5-oxa-2-selena-8-telluranonane (XIf),
6% of 1,4-oxatellurane (VIIc), and traces of 1-chloro-
3-oxa-6-telluraheptane (XIIc).
From oligomer VI we obtained 6% of 5-oxa-2,8-di-
selenanonane (XIb), 9% of 5-oxa-2,8-ditelluranonane
(XIc), 31% of 5-oxa-2-selena-8-telluranonane (XIf),
8% of 1,4-oxaselenane (VIIb), and 10% of 1,4-oxatel-
lurane (VIIc).
1
Compound XIf. H NMR spectrum, δ, ppm: 1.90 s
The reaction with a mixture of dimethyl disulfide
and dimethyl diselenide under milder conditions (see
text) gave 18% of XIa, 27% of XIb, 42% of XId, 15%
of 1-chloro-3-oxa-6-thiaheptane (XIIa), and 14% of
1-chloro-3-oxa-6-selenaheptane (XIIb). Mass spec-
trum of XIIa, m/z (35Cl): 154 [M]+·, 118 [M – HCl]+,
93 [M – CH3SCH2]+, 75 [CH3SCH2CH2]+, 63
[CH2CH2Cl]+, 61 [CH3SCH2]+, 49 [CH2Cl]+, 47
[CH3S]+, 45 [CHS]+, [CH2CH2OH]+, 43 [C2H3O]+, 41
[C2HO]+. Mass spectrum of XIIb, m/z (35Cl): 202
[M]+·, 123 [CH3SeCH2CH2]+, 109 [CH3SeCH2]+, 95
[CH3Se]+, 93 [CHSe]+, 63 [CH2CH2Cl]+, 45
[CH2CH2OH]+, 43 [C2H3O]+, 41 [C2HO]+.
2
(3H, CH3Te, JH, Te = 21 Hz), 2.01 s (3H, CH3Se,
2JH,Se = 10 Hz), 2.66 t (2H, CH2Se), 2.76 t (2H, CH2Te,
2JH,Te = 26 Hz), 3.68 t (2H, OCH2CSe, JHH = 7.2 Hz),
3
3.74 t (2H, OCH2CTe, 3JHH = 7.5 Hz). C NMR spec-
13
1
trum, δC, ppm: –22.01 (CH3Te), 2.69 (CH2Te, JC,Te
=
1
117 Hz), 4.64 (CH3Se, JC,Se = 63 Hz), 24.33 (CH2Se,
1JC,Se = 62 Hz), 70.54 (OCH2CSe), 72.57 (OCH2CTe).
Mass spectrum, m/z (I/Itot, %): 312 (5.4) [M]+·, 297
(13.1), 225 (9.6), 145 (14.1), 123 (9.3), 107 (6.2), 95
(12.4), 43 (2.7), 41 (19.2). Found, %: C 23.01; H 4.58;
Se+Te 66.86. C6H14OSeTe. Calculated, %: C 23.33;
H 4.51; Se+Te 66.94.
b. Dimethyl dichalcogenide (Me2S2, Me2Se2, or
Me2Te2) was dissolved in the system hydrazine hy-
drate–KOH on heating to 80–85°C, and a required
amount of compound I was slowly added to the result-
ing solution or to a mixture of solutions containing
equimolar amounts of two dimethyl dichalcogenides,
maintained at 50°C. The mixture was stirred for 2.5 h
at 60–65°C, and the organic layer was separated,
analyzed by GC–MS, and subjected to vacuum distilla-
tion. The reaction with dimethyl disulfide gave 66% of
5-oxa-2,8-dithianonane (XIa), the reaction with di-
methyl diselenide gave 68% of 5-oxa-2,8-diselena-
nonane (XIb), and dimethyl ditelluride gave rise to
60% of 5-oxa-2,8-ditelluranonane (XIc) and 5% of
1,4-oxatellurane (VIIc).
6-Oxa-3,9-diselenaundecane (XIg). A mixture of
0.19 g (0.0008 mol) of 1,4,5-oxadiselenepane (VIIIb),
0.28 g (0.005 mol) of potassium hydroxide, and 1.8 g
(0.036 mol) of hydrazine hydrate was stirred for 2.5 h
at 76–80°C. The mixture was cooled to room tempera-
ture, 0.73 g (0.006 mol) of ethyl bromide was slowly
added, and the mixture was stirred for 0.5 h at 35–
40°C, cooled to room temperature, and extracted with
methylene chloride. The extract was dried over MgSO4,
and the solvent was removed. The residue, 0.17 g, was
identified as 6-oxa-3,9-diselenaundecane (XIg) on the
1
basis of the GLC, H and 13C NMR, GC–MS, and
analytical data. 1H NMR spectrum, δ, ppm: 1.39 t (3H,
CH3), 2.55 q (2H, CH2Se), 2.72 t (2H, CH2Se), 3.68 t
(2H, OCH2). 13C NMR spectrum, δC, ppm: 15.79
(CH3), 17.57 (CH2Se), 22.19 (SeCH2), 71.13 (OCH2).
Mass spectrum, m/z (I/Itot, %): 290 (1.7) [M]+·, 261
(10.7) [M – C2H5]+, 189 (10.9), 151 (3.3), 137 (10.3),
109 (22.9), 93 (8.1), 55 (11.5), 45 (4.5), 41 (3.7).
Found, %: C 33.62; H 6.18; Se 55.01. C8H18OSe2. Cal-
culated, %: C 33.33; H 6.25; Se 54.86.
Under analogous conditions, from a mixture of di-
methyl disulfide and dimethyl diselenide we obtained
52% of 5-oxa-2,8-dithianonane (XIa), 34% (calculated
on the initial dimethyl diselenide) of 5-oxa-2,8-di-
selenanonane (XIb), and 62% of 5-oxa-2-thia-8-se-
lenanonane (XId).
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REACTIONS OF β,β′-DICHLORODIETHYL ETHER WITH ELEMENTAL CHALCOGENS
51
9. Korchevin, N.A., Russavskaya, N.V., Alekmin-
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