Synthesis of polydentate chalcogen-containing ligands using the system hydrazine hydrate–base

Article abstract of DOI:10.1134/S1070363217030069

The reaction of dichlorodiethyl ether or dichlorodiethylamine hydrochloride with potassium or ethanolammonium dichalcogenides prepared in situ from elemental sulfur or selenium in the system hydrazine hydrate–alkali results in oligomeric dichalcogenides,

Full text of DOI:10.1134/S1070363217030069

ISSN 1070-3632, Russian Journal of General Chemistry, 2017, Vol. 87, No. 3, pp. 396–401. © Pleiades Publishing, Ltd., 2017.
Original Russian Text © Е.P. Levanova, А.I. Vilms, V.А. Bezborodov, I.А. Babenko, N.G. Sosnovskaya, N.V. Istomina, А.I. Albanov, N.V. Russavskaya,
I.B. Rozentsveig, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 3, pp. 387–392.
Synthesis of Polydentate Chalcogen-Containing Ligands
Using the System Hydrazine Hydrate–Base
Е. P. Levanovaa*, А. I. Vilmsb, V. А. Bezborodovb, I. А. Babenkob, N. G. Sosnovskayac,
N. V. Istominac, А. I. Albanova, N. V. Russavskayaa, and I. B. Rozentsveiga
a Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
*e-mail: venk@irioch.irk.ru
b Irkutsk State University, Irkutsk, Russia
cAngarsk State Technical University, Angarsk, Russia
Received October 20, 2016
Abstract—The reaction of dichlorodiethyl ether or dichlorodiethylamine hydrochloride with potassium or
ethanolammonium dichalcogenides prepared in situ from elemental sulfur or selenium in the system hydrazine
hydrate–alkali results in oligomeric dichalcogenides, whose further splitting at the chalcogen–chalcogen bond
in the same system and subsequent alkylation affords bis(organylsulfanyl)- or bis(organylselanyl)-substituted
derivatives of diethyl ether or diethylamine. Ligands with aryl substituents at the chalcogens have been
prepared in 48-59% yield by splitting of diaryldichalcogenides in the system hydrazine hydrate–alkali and
subsequent reaction with dichlorodiethyl ether or dichlorodiethylamine. A ditopic tetradentate ligand has been
synthesized by the use of dichlorodiethylformal.
Keywords: sulfur, selenium, dichalcogenides, polydentate ligands, hydrazine hydrate
DOI: 10.1134/S1070363217030069
The chalcogen atoms in organic molecules are
capable of formation of strong coordination bonds with
heavy metal ions [1]. Especially stable chelate
complexes are formed when two or more donor centers
are present in the ligand [1]. Complexes of this type
are of interest for coordination chemistry [2, 3], for the
design of analytical reagents [4] and selective sensors
[5–7] and are used for the analysis and investigation of
coordination compounds of noble metals [8].
Especially promising is the use of metal complexes
with chalcogen-containing ligands in homogeneous
catalysis [9, 10]. Thus, palladium complexes with
organochalcogen ligands were proposed as catalysts in
the Suzuki reaction [11]. An important feature of
complexes used in homogeneous catalysis is their
ability to reduce the coordination number of the
complex-forming metal [12]. As a result, coor-
dinatively unsaturated complexes are formed, which
can interact with the molecules of the reagents to
continue the catalytic cycle. Since the chalcogen
atoms, as soft bases, form strong bonds with many
transition metal ions (soft acids), for the formation of
labile metal–ligand bonds the presence of hard donor
centers in the structure of the latter is necessary, for
example, the oxygen or nitrogen atoms.
These requirements are fulfilled in polydentate
ligands containing between the donor atoms the chain
of two carbon atoms, which favors the formation of the
energetically stable five-membered chelate cycles
upon the formation of complexes with metals. Within
this group of ligands the derivatives of diethyl ether
and diethylamine containing additional chalcogenide
substituents are intensively studied [3, 4, 6–11]. The
data on the synthesis of oxa- and aza-substituted
bischalcogenide ligands of this type are scarce. The
known methods are mostly based on the use of 2,2'-
dichloroethyl ether (chlorex) 1а and the salts of 2,2'-
dichlorodiethylamine 1b as the reagents. A multistep
synthesis of bis(2-methylsulfanyl)diethylether in 61%
yield from chlorex via the steps of formation of the
double isothiuronium salt with its subsequent trans-
formation to the corresponding dithiol and methylation
of the latter with methyl iodide has been described
396

SYNTHESIS OF POLYDENTATE CHALCOGEN-CONTAINING LIGANDS
397
[13]. For the synthesis of dibenzylsulfanyl derivative
instead of chlorex diethylene glycol ditosylate is used,
whose reaction with benzylthiuronium chloride in the
presence of solid alkali and a phase transfer catalyst
gives the target product in 30–55% yield [14].
Dichalcogen-substituted derivatives of diethylamine
were prepared in 69–89% yield by the reaction of
dichlorodiethylamine with thiolates or selenolates of
alkali metals [5, 6, 10, 11, 15–21]. For the synthesis of
reaction an excess of alkali was used, R2Y2 : KОН =
1 : 5. Chalcogenolates 3а–3c either were not isolated
as individuals.
Scheme 2.
2R2Y2 + N2H2·H2O + 4KOH → 4RYK + N2 + 5H2O,
3a–3c
R = Ph, Y = S (a), Se (b); R = Bn, Y = S (c).
Alkylchalcogenide tridentate ligands 2а–2f were
obtained using active forms of chalcogens prepared as
in Scheme 1. Polycondensation of dihaloderivatives 1а
and 1b with dichalcogenide anions gives oligomeric
dichalcogenides 4а–4d (Scheme 3).
bisphenylselanyl
derivative
of
3-azapentylene
diphenyldiselenide was used, which was reduced to
phenylselenolate by the reaction with NaBH4 [6]. All
reactions with thiolates and selenolates were carried
out in inert atmosphere. The above brief inventory of
the methods of synthesis of bischalcogenyl-substituted
derivatives of diethyl ether and diethylamine shows
that they are laborious and that elaboration of
synthetically efficient methods for preparation of
polydentate ligands containing oxa- or aza-groups in
the molecule, as well as with two organylsulfanyl or
-selanyl moieties is actual.
Scheme 3.
nY22−
Х
Х
Y
Cl
Cl
_2nCl−
Y
n
4a_4d
1a, 1b
1, X = O (a), NH (b); 4, X = O, Y = S (a), Se (b); X = Nh,
Y = S (c), Se (d).
In the present work two methods of the synthesis
of 1,5-diorganylchalcogenide-3-oxa(3-aza)pentylenes
2а–2j are worked out based on the use of chlorex 1а or
dichlorodiethylamine hydrochloride 1b, elemental
sulfur, selenium or diorganyldichalcogenides in the
system hydrazine hydrate–base.
The reductive splitting of oligomers 4а–4d at the
Y–Y bond using the system hydrazine hydrate–KOH
results in the formation of dichalcogenolates 5а–5d,
which were further alkylated with alkyl halides
affording the target products 2а–2f (Scheme 4).
Scheme 4.
Elemental chalcogens and diorganyldichalcogenides
in the system hydrazine hydrate–base are reduced to
polychalcogenides or potassium organylchalcogenolates
[22]. The reduction of sulfur or selenium to disulfide
or diselenide anion proceeds rather selectively using
either the system hydrazine hydrate–monoethanolamine
(molar ratio N2H4·H2O : H2NCH2CH2OH = 10 : 1) or
the system hydrazine hydrate–KOH with the molar
ratio Y : KOH=1 : 1 [22] (Scheme 1).
N2H4 H2O, KOH
4a_4d
Х
KY
YK
5a_5d
Х
CH3I or C2H5Br
_KI or KBr
RY
YR
2a_2f (56_74%)
5, X = O, Y = S (a), Se (b); X = NH, Y = S (c), Se (d); 2,
X = O, Y = S, R = CH3 (a), C2H5 (b), Y = Se, R = CH3 (c),
C2H5 (d); X = NH, Y = S, R = CH3 (e), Y = Se, R = CH3 (f).
Scheme 1.
Oligomeric dichalcogenides 4а, 4b we obtained
earlier [23, 24] when studying the reactions of dielec-
trophiles (including chlorex) with elemental chalco-
gens in the system hydrazine hydrate–base. Oligomer
4а was obtained in 62% yield and had the average
molecular mass equal to 1770, as defined by the
method of terminal groups [23]. Oligomer 4b was
isolated in 75% yield and had molecular mass of 1730
[24]. The structure of the obtained oligomers was
proved by the method of reductive splitting. The
synthesis and reductive splitting of oligomers 4c, 4d is
performed for the first time. The compounds are
viscous black substances. Oligomer 4c was obtained in
4Y + 4KOH + N2H4·H2O → 2K2Y2 + N2 + 5H2O,
4Y + N2H4·H2O + 4HOCH2CH2NH2
→ 2(HOCH2CH2NH3)2Y2 + N2 + H2O,
4Y + 5N2H4·H2O → 2(N2H5)2Y2 + N2 + 5H2O,
Y = S, Se.
The obtained anionic forms of chalcogens were used
in further syntheses without isolation as individuals.
The reductive splitting of diorganyldichalcogenides
proceeds by Scheme 2. For effective proceeding of the
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 3 2017

398
LEVANOVA et al.
Table 1. Yields, boiling points, elemental analysis, and IR spectra of compounds 2а–2j
Found, %
Calculated, %
Comp. Yield,
bp, °C
(mmHg)
Formula
IR spectrum, ν, cm-1
no.
%
C
H
N
–
Y
C
H
N
–
Y
2а
60
87–90 (3)
{97 (4) [13]}
43.19 8.51
38.89 C6H14OS2
32.47 C8H18OS2
43.33 8.49
38.56 2970, 2916, 2860
2b
2c
2d
2e
2f
67
93–96 (2) [23] 49.54 9.27
–
–
–
49.44 9.34
–
–
–
32.99 2985, 2936, 2914,
2886, 2854
64 96–97 (1.5) [24] 27.60 5.39
64 112–116 (1.5) 33.59 6.12
60.81 C6H14OSe2 27.71 5.42
55.00 C8H18OSe2 33.35 6.30
60.72 2994, 2970, 2925,
2858
54.80 2973, 2956, 2945,
2865
74 85–87 (1.5) [3] 43.60 9.00 8.32 39.08 C6H15NS2
43.59 9.15 8.47 38.79 3283, 2962, 2921,
2815
56
57
58
64
119–122 (2) 27.91 5.87 5.56 60.66 C6H15NSe2 27.81 5.83 5.41 60.95 3287, 2994, 2962,
2922, 2820
2g
2h
2i
203–206 (1.5) 65.80 6.02
–
–
–
21.15 C16H18OS2 66.17 6.25
19.69 C18H22OS2 67.88 6.96
41.28 C16H18OSe2 50.02 4.72
–
–
–
22.08 3072, 3056, 3019,
2958, 2925, 2864
120 (0.02)
[3, 14]
67.64 6.97
50.45 4.51
20.13 3083, 3060, 3027,
2952, 2917, 2859
–
41.10 3069, 3054, 3015,
2978, 2934, 2860
2j
46 213–215 (2) [5] 66.37 6.82 4.93 21.88 C16H19NS2 66.39 6.62 4.84 22.15 3300, 3056, 3018,
2922, 2832
70% yield with molecular mass 1460, oligomer 4d in
96% yield and molecular mass 6400. Therefore, we
have realized the preparative synthesis of compounds
2а–2f via the intermediate dichalcogenide oligomers.
Using the approach represented in Schemes 1, 3,
and 4, we have first synthesized a ditopic tetradentate
ligand, 1,10-dithia-5,7-dioxaundecane 5 by the reaction
of 2,2-dichlorodiethylformal 6 and sulfur preliminary
reduced in the system hydrazine hydrate–monoethanol-
amine via the stage of formation of oligomeric
disulfide 7 (Scheme 6). Oligomer 7 was prepared in
94% yield as a highly viscous gray substance; its
For the synthesis of arylchalcogenide and benzyl-
chalcogenide ligands 2g–2j we have used an alter-
native approach based on the reaction of chalco-
genolates 3а–3c with chlorex 1а or with dichloro-
diethylamine hydrochloride 1b (Scheme 5). The yields,
data of elemental analysis and IR spectroscopy of
Scheme 6.
1
O
O
n
compounds 2а–2j are given in Table 1, the data of H
Cl
Cl
and 13С NMR spectra, in Table 2.
6
nS22−
Scheme 5.
O
O
SS
_2nCl−
Х
n
+ RYK
7 (94%)
Cl
Cl
3a_3c
1a, 1b
N2H4 H2O, KOH
Х
O
O
RY
YR
KS
SK
2g−2j (46_64%)
1, X = O (a), NH (b); 2, X = O, Y = S, R = Ph (g), Bn (h),
Y = Se, R = Ph (i), X = NH, Y = S, R = Ph (j); 3, R = Ph,
Y = S (a), Se (b); R = Bn, Y = S (c).
2CH3I
_2KI
O
O
CH3S
SCH3
5 (64%)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 3 2017

SYNTHESIS OF POLYDENTATE CHALCOGEN-CONTAINING LIGANDS
Table 2. 1H, 13C, 77Se NMR spectra of compounds 2а–2j, chemical shifts, δ, ppm
399
δН, ppm
δС, ppm
Comp.
no.
δSe, ppm
XCH2
3.64 t
YCH2
2.67 t
NH
–
R
XCH2
70.15
YCH2
R
2а
33.40
15.90 (CH3)
–
–
2.14 s (3H, CH3)
3J = 6.8 Hz
2b
3.62 t
2.71 t
–
–
–
70.54
70.68
30.87
24.07
26.26 (CH2), 14.73
(CH3)
2.57 q (2H, CH2),
2.49 t (3H, CH3, 3J =
7.4 Hz)
3J = 7.0 Hz
2c
2d
2e
3.69 t
2.70 t
2.03 s (3H, CH3)
4.48 d (CH3, 1JSeC
=
60.24
175.16
–
61.9 Hz)
3J = 7.0, 2JSeH = 12.5 Hz
3.68 t
2.72 t
2.60 q (2H, CH2, 71.00
3J = 7.5 Hz), 1.39 t
22.06 d 17.53 d (CH2, 1JSeC
(1JSeC
58.5 Hz), 15.73 (CH3)
=
=
(3H, CH3, 3J = 7.5 Hz)
65.0 Hz)
3J = 7.3 Hz
2.84 t
2.66 t
1.56 br.s 2.10 s (3H, CH3)
1.75 br.s 1.94 s (3H, CH3)
47.55
48.39
34.33
15.27 (CH3)
3J = 6.6 Hz
2f
2.83 t
2.64 t
25.79 d 3.92 d (CH2, 1JSeC
(1JSeC
62.3 Hz)
=
49.4
–
=
3J = 6.7 Hz
60.8 Hz)
2g
3.60 t
3.06 t
–
–
–
7.13–7.33 m (5H, 69.69
C6H5)
33.23
135.92 (Ci), 129.53,
128.97 (Co, Cm),
126.25 (Cp)
3J = 6.9 Hz
2h
2i
3.51 t
2.57 t
3.71 s (2H, CH2Ph), 70.40
7.21–7.30 m (5H,
C6H5)
30.60
138.32 (Ci), 128.88,
128.46 (Co, Cm),
126.98 (Cp)
–
270.2
–
3J = 6.7 Hz
3.64 t
3.00 t
7.20–7.50 m (5H, 70.40
C6H5)
26.59 d 129.44 (Ci), 132.58,
(1JSeC
128.98 (Co, Cm),
65.0 Hz) 126.90 (Cp)
=
3J = 7.1 Hz
2j
2.61 t
3.03 t
1.80 br.s 7.33 m (2H, Ho), 7.24 47.73
m (2H, Hm), 7.17 m
34.19 135.28 (Ci), 129.78,
128.92 (Co, Cm),
126.26 (Cp)
3J = 6.4 Hz
(1H, Hp)
molecular mass was about 1000. The splitting of
oligomer 7 at the S–S bonds and the subsequent
alkylation results in the formation of compound 5.
EXPERIMENTAL
IR spectra were recorded on a Bruker IFS-25
spectrophotometer from thin layers. 1Н, 13С, 77Se NMR
spectra were registered on a Bruker DPX-400
spectrometer (400.13, 100.62, and 76.31 MHz
respectively) in DMSO-d6 or CDCl3 solution, internal
reference TMS (1Н, 13С) and Me2Se (77Se). Mass
spectra were taken on a Shimadzu GCMS–QP5050A
Therefore, the use of basic-reductive systems on
the basis of hydrazine hydrate allows synthesizing
dichalcogenide polydentate ligands of linear structure,
promising reagents for the design of chelate complexes
with participation of heavy metal ions.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 3 2017

400
LEVANOVA et al.
chromatomass spectrometer (column SPB-5, 60000×
0.25 mm, quadruple mass analyzer, electron ionization,
70 eV, temperature of ion source 190°С, the range of
detected masses 34–650 Da). The purity of the
products and the course of the reactions were
monitored by GC on a LKhM 80-MD-2 chromato-
graph (column 2000×3 mm, liquid phase DC-550, 5%
on Chromaton N-AW-HMDS, linear programming of
the temperature with the heating rate 12 deg/min, gas
carrier helium).
extracted with ether (2×50 mL), the extract was dried
over MgSO4, the solvent was removed, the residue was
distilled in a vacuum.
Compounds 2g–2j (general procedure). 20%
KOH solution in hydrazine hydrate and the calculated
amount of diorganyl dichalcogenide R2Y2 (R2Y2 :
KOH = 1 : 5) was stirred for 4 h at 85–90°C. the
reaction mass was cooled to 60°C, 1 equivalent of
chlorex 1а or salt 1b was added, the mixture was
stirred for 5 h at 60–70°C, cooled to 25°C, the product
was extracted with ether (2×50 mL), the extract was
dried over MgSO4, the solvent was removed.
Compounds 2g, 2j were distilled in a vacuum,
compounds 2h, 2i were analyzed without distillation.
Oligomers 4а,b were synthesized as described
earlier [23, 24]. The oligomers were also prepared by
the use of the system hydrazine hydrate–mono-
ethanolamine [25].
Poly(3-azapentylene disulfide) (4c). To the solu-
tion of 1.26 g (0.0224 mol) of KOH and 1.1 mL of
hydrazine hydrate in 7 mL of water 0.72 g
(0.0224 mol) of elemental sulfur was added by
portions, the reaction mass was stirred for 5 h at 85–
90°С, cooled, 6 mL of 10% KOH and 2.0 g
(0.0112 mol) of dichlorodiethylamine hydrochloride
1b was added. The obtained mixture was stirred for 2 h
at 60–65°С, cooled, the formed oligomer was
separated by decanting, washed with water, ethanol,
ether, dried in a vacuum to a constant mass. 1.13 g
(75%) of oligomer 4c was obtained as a viscous
compound of black color. IR spectrum, ν, cm–1: 3291,
2920, 2820, 1455, 1358, 1285, 1122, 1003, 752.
Found, %: С 34.96, Н 6.67, Cl 4.86, N 10.61, S 43.63.
С44Н98N11Cl2S20. Calculated, %: С 35.41, Н 6.57, Cl
4.76, N 10.33, S 42.92. The molecular mass
determined by the residual chlorine was 1460, which
corresponded to n = 11.
Poly(3,5-dioxaheptylenedisulfide) (7). 3 mL of
hydrazine hydrate, 0.34 g (0.0056 mol) of ethanol-
amine, and 1.12 g (0.035 mol) of elemental sulfur was
stirred for 2.5 h at 60–65°C. The reaction mass was
cooled to 25°C, 3.0 g (0.0173 mol) of dichlorodiethyl-
formal was added dropwise and the mixture was stirred
for 4 h at 75–80°C. After cooling, oligomer 7 was
separated by decantating as a viscous mass. Yield 2.7 g
(94%). IR spectrum, ν, cm–1: 2921, 2870, 2801, 1466,
1412, 1377, 1282, 1197, 1154, 1115, 1072, 1029, 951,
1
812, 791, 758, 666, 620, 477. H NMR spectrum
(DMSO-d6), δ, ppm: 2.93 m (4H, CH2S), 3.73 m (4H,
CCH2O), 4.66 s (2H, OCH2O). 13C NMR spectrum
(DMSO-d6), δ, ppm: 38.14 (CH2S), 65.56 (CCH2O),
94.62 (OCH2O). Found, %: C 35.50, H 6.27, S 29.05,
Cl 7.79. C27.5H55Cl2S9. Calculated, %: C 36.26, H 6.04,
S 31.65, Cl 7.80. The molecular mass determined by
the residual chlorine was 910, which corresponded to
n = 5–6.
Poly(3-azapentylenediselenide) (4d) was prepared
similarly. Yield 3.28 g (96%) of oligomer 4g as a
viscous mass of black color. IR spectrum, ν, cm–1:
3283, 2921, 2815, 1455, 1407, 1356, 1261, 1221, 1179,
1116, 975, 797, 735, 643, 547. Found, %: С 20.61, Н
4.11, Cl 1.11, N 5.90, Se 69.39. С112Н252N28Cl2Se54.
Calculated, %: С 20.98, Н 3.96, Cl 1.12, N 6.12, Se
68.94. The molecular mass determined by the residual
chlorine was 6400, which corresponded to n = 28.
5,7-Dioxa-2,10-dithiaundecane (5). A mixture of
2.97 g (0.053 mol) of KOH, 13 mL of hydrazine
hydrate, and 1.76 g (0.0106 mol) of oligomer 7 was
stirred for 3 h at 85–90°C. The reaction mass was
cooled to 25°C, 4.52 g (0.0318 mol) of methyl iodide
was added dropwise, the mixture was stirred for 2 h at
30–35°C and 4 h at 25°C. The product was extracted
with ether (2×50 mL), the extract was dried over
MgSO4 and evaporated. The residue was distilled in a
vacuum. Yield 1.33 g (64%), colorless liquid, bp 102–
105 (2 mmHg). IR spectrum, ν, cm–1: 2918, 2873,
2792, 1463, 1428, 1380, 1287, 1203, 1155, 1112,
Compounds 2а–2f (general procedure). 20%
KOH solution in hydrazine hydrate and the calculated
amount of oligomer 4а–4d (molar ratio n : KOH = 1 : 5)
was stirred for 3.5 h at 85–90°C, the reaction mass was
cooled to 25°C and MeI or EtBr was added dropwise
[n : AlkHlg = 1 : (2.2–3)] and the mixture was stirred
for 2.5 h at 30–35°C and 4 h at 25°C. The product was
1
1074, 1027, 954, 775, 726, 698, 659, 618, 475. H
NMR spectrum (CDCl3), δ, ppm: 2.14 s (6H, CH3),
3
2.71 t (4H, J 6.6 Hz, CCH2O), 4.72 s (2H, OCH2O).
13C NMR spectrum (CDCl3), δ, ppm: 15.88 (CH3),
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 3 2017

SYNTHESIS OF POLYDENTATE CHALCOGEN-CONTAINING LIGANDS
401
11. Kumar, S., Rao, G.K., Kumar, A., Singh, M.P., and
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33.85 (CH2S), 66.88 (CCH2O), 95.31 (OCH2O). Mass-
spectrum, m/z: 196 [M]+, 75 [CH3SCH2CH2]+. Found,
%: C 42.67, H 8.42, S 32.10. C7H16O2S2. Calculated,
%: C 42.86, H 8.21, S 32.66.
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