Synthesis of unsaturated organochalcogen compounds proceeding from dichloroethenes and organyl dichalcogenides

Article abstract of DOI:10.1134/S107042801708005X

Reaction of 1,1- and 1,2-dichloroethenes with Ph₂S₂, Ph₂Se₂, Bn₂S₂, and i-Pr₂S₂ in a system hydrazine hydrate–KOH proceeds as a sequence of successive transformations: dehydrochlorination of initial dichloroethenes to form chloroacetylene, chlorine substitution for the chalcogen-containing nucleophile (ethynylchalcogenides formation), and the addition of the nucleophilic reagent to the triple bond affording 1,2- dichalcogenylethenes. In reactions with PhS^– and PhSe^? nucleophiles due to the high rate of all stages 1,2-bis (phenylchalcogenyl)ethenes are obtained having mainly the Z-configuration. In reactions with BnS^? and i-PrS^? in the IR, NMR and chromato-mass spectra intermediate ethynylchalcogenides were identified, and the final products consisted of a mixture with the prevalence of the Z-isomer.

Full text of DOI:10.1134/S107042801708005X

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2017, Vol. 53, No. 8, pp. 1186–1190. © Pleiades Publishing, Ltd., 2017.
Original Russian Text © E.P. Levanova, V.S. Nikonova, I.B. Rosentsveig, N.V. Russavskaya, A.I. Albanov, N.A. Korchevin, 2017, published in Zhurnal
Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1172–1176.
Synthesis of Unsaturated Organochalcogen Compounds
Proceeding from Dichloroethenes and Organyl Dichalcogenides
E. P. Levanova, V. S. Nikonova, I. B. Rosentsveig, N. V. Russavskaya,
A. I. Albanov, and N. A. Korchevin*
Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences,
ul. Favorskogo 1, Irkutsk, 664033 Russia
*e-mail: venk@irioch.irk.ru
Received April 12, 2017
Abstract—Reaction of 1,1- and 1,2-dichloroethenes with Ph2S2, Ph2Se2, Bn2S2, and i-Pr2S2 in a system
hydrazine hydrate – KОН proceeds as a sequence of successive transformations: dehydrochlorination of initial
dichloroethenes to form chloroacetylene, chlorine substitution for the chalcogen-containing nucleophile
(ethynylchalcogenides formation), and the addition of the nucleophilic reagent to the triple bond affording 1,2-
dichalcogenylethenes. In reactions with PhS– and PhSe‒ nucleophiles due to the high rate of all stages 1,2-bis
(phenylchalcogenyl)ethenes are obtained having mainly the Z-configuration. In reactions with BnS‒ and i-PrS‒
in the IR, NMR and chromato-mass spectra intermediate ethynylchalcogenides were identified, and the final
products consisted of a mixture with the prevalence of the Z-isomer.
DOI: 10.1134/S107042801708005X
Unsaturated organochalcogen compounds are
important synthons in organic synthesis [1, 2]. Besides
the multiple bonds and chalcogen atoms contained in
organic molecules may behave as effective π- and n-
donors in coordination with transition metal ions thus
providing a possibility of designing bifunctional
ligands for complex formation [3, 4].
14% at the UV-irradiation of a mixture (PhS)2Hg with
Z- or E-1,2-dichloroethene in DMSO, and regardless
of the configuration of the initial dichloroethene the
reaction product formed as an isomers mixture
(E/Z 0.4) [6]. When in the reaction were used
preliminary prepared E- or Z-isomers ClCH=CHSPh,
under the same conditions the yield of 1,2-bis-
(phenylsulfanyl)ethene reached 81–84% (the ratio of
E- and Z-isomers in the reaction products obtained
from both initial isomers was 0.5) [6].
Chalcogen-substituted ethenes belong to the
simplest organochalcogen structures, where at the
presence of two chalcogen atoms in the 1, 2 positions
the Z- or E-mutual position of the chalcogenyl
fragments is strictly fixed. Their Z-position with
respect to the double bond is favorable for the
formation of coordination compounds. Yet the lack of
simple and stereoselective methods of the synthesis of
this type ligands impedes the development of the
corresponding part of the coordination chemistry and
as a consequence the preparation of new efficient
extractants, homogenic catalysts, and reagents for
organic synthesis.
The reaction of 1,2-dibromoethene and PhSCu in
quinoline with added 2–10% of pyridine at 200°С
provided 1,2-bis(phenylsulfanyl)ethene in a 50% yield
(the ratio of E- and Z-isomers 2.3) [7]. The addition of
anions PhSe‒ (generated from Ph2Se2 and NaBH4 in
polyethylene glycol PEG-400) to ethynylselanyl-
benzene resulted in a selective formation of E-isomer
1,2-bis(phenylselanyl)ethene in a 20% yield [8].
The application of metal complex catalysis which is
extensively used in the formation of С–chalcogen
bonds [9] only once was utilized in the synthesis of
dichalcogenyl-substituted ethenes free of other substi-
tuents [10], in the presence of the complex (bipy)2NiBr2
from 1,2-dibromoethene and PhSeNa (prepared from
Ph2Se2 and NaBH4) 1,2-bis(phenylselanyl)ethene
The first specimens of 1,2-dichalcogenylethenes
were obtained from 1,2-dichloroethene and organic
sulfides [5], yet the yields and configurations of the
prepared compounds were not reported. 1,2-Bis-
(phenylsulfanyl)ethene formed in a yield of only 5–
1186

SYNTHESIS OF ORGANOCHALCOGEN COMPOUNDS PROCEEDING
1187
(the configuration of the product not reported) formed
in a 70% yield.
final reaction products 3 (Scheme 2, stages c, d). The
addition of RY‒ anions to the triple bond occurs to the
β-position since the forming carbanion 6 is stabilized
with the contiguous chalcogen atom.
In the synthesis of 1,2-bis(benzylsulfanyl)ethene a
difficultly accessible sodium 1,2-ethenedithiolate was
utilized [11]. 1,2-Bis(benzylselanyl)ethene was obtained
in a 95% yield by the reaction of dibenzyldiselenide
with acetylene in a pressure reactor (12 at) [12]. In the
course of structural transformations of dialkylacetals of
sulfanyl-substituted acetaldehydes in the plesence of
sulfuric or polyphosphoric acids or zinc chloride 1,2-
bis(phenylsulfanyl)- and 1,2-bis(benzylsulfanyl)-
ethenes were formed [13].
Scheme 2.
.
b. 2a_2d
_KCl
a. N2H4 H2O/KOH
1a, 1b
Cl
YR
_KCl
5
4
_
_
d. H2O
_
c. RY
3a_3d
_OH
RY
YR
6
We showed that 1,2-dichalcogenylethenes
formed in the reactions of diorganyl dichalcogenides
R2Y2 with 1,1-dichloroethene 1а or 1,2-dichloroethene
(mix-ture of E-, Z-isomers, ~1 : 1) 1b in a system
hydrazine hydrate – KОН. In this system dichalco-
genides R2Y2 suffer a reductive cleavage at the Y–Y
bond giving potassium chalcogenolates 2a–2d [14].
The prepared solutions of potassium chalcogenolates
in hydrazine hydrate were used in subsequent
syntheses without isolation of compounds 2a–2d.
Vinylidene chloride 1а and 1,2-dichloroethene 1b
react with chalcogenolates 2a–2d affording as
final products 1,2-dichalcogenylethenes 3a–3d
(Scheme 1).
Compounds 3a and 3d (R = Ph) according to NMR
data consist of a single isomer. GC-MS shows that
compound 3а contains traces (<1%) of the second
isomer. Dichalcogenylethene 3b forms as a mixture of
isomers in a ratio 10 : 1, and compound 3с also
contains two isomers in a ratio 5 : 1.
According to the rule of the nucleophilic addition to
acetylenes the formed adduct should possess the Z-
configuration [16]. The analysis of satellite signals (Н–
1
С13) in the Н NMR spectra of compounds 3a–3c
(major isomer) shows that the coupling constant in the
ethenyl fragment 3J(HC12–C13H) is 8.1‒8.5 Hz,
corresponding to the Z-position of hydrogen atom and
chalcogenyl substituent [17]. The mixture of E- and Z-
isomers 3b was separated by fractional crystallization
from ethanol [7], E-isomer was obtained as crystals, Z-
isomer, as oily fluid. Compound 3a that we isolated
both in the reaction with vinylidene chloride 1a and
with 1,2-dichloroethene 1b was a light red fluid whose
boiling point was in agreement with the data of [7].
Therefore it is presumable that compounds 3a and 3d
form as Z-isomers, and in compounds 3b and 3c the Z-
isomer prevails. The formation of a small amount of E-
isomers in these cases probably is due to the steric
hindrances from the groups i-Pr and Bn.
Scheme 1.
.
2R2Y2 + N2H4 H2O + 4KOH
4RYK + N2 + 5H2O
2a_2d
Cl
+
2 2a_2d
RYCH=CHYR
Cl
_2KCl
1a
3a_3d
Cl
+
2 2a, 2b, 2d
3a, 3b, 3d
Cl
_2KCl
1b
Y = S, R =Ph (a), Bn (b), i-Pr (c); Y = Se, R = Ph. (d).
As follows from Scheme 3, the transformation 5 →
3 is governed by the reactivity of nucleophiles RY–
and by the stability of the intermediate carbanion 6; the
latter in its turn depends on the stabilizing effect of the
chalcogenyl substituent. We showed in [18] that the
stabilizing effect of the chalcogene-containing group
decreased in the series PhS– > PhSe– > BnS–. Therefore
it is presumable that the reaction in question 5 → 3
effectively proceeds with RY- = PhS– and PhSe–, but
with RY– = BnS– and i-PrS– the reaction is impeded.
Evidently it is the reason of the appearance in the
The formation of one type compounds suggests that
presumably in the intermediate stages in the system
hydrazine hydrate–KОН first dehydrochlorination of
compounds 1a and 1b occurs furnishing chloro-
acetylene 4 (Scheme 2, stage а). The cleavage of HCl
from dichlorides 1a and 1b at the action of bases is
well known [15]. Chloroacetylene 4 is a highly
reactive compound where the chlorine atom is readily
substituted by RY‒ anions (Scheme 2, stage b). The
arising ethynylchalcogenides 5 add chalcogenolate
anions to the triple bond leading to the formation of the
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 8 2017

LEVANOVA et al.
1188
reaction products of Bn2S2 (with compound 1a and 1b)
and i-Pr2S2 (only reaction with 1a was performed) of a
considerable amount of the corresponding ethynyl-
quencies 400.13, 100.62, and 76.31 МHz respectively)
in CDCl3, internal reference TMS (1Н, 13С), Me2Se
(77Se). Mass spectra were taken on a GC-MS
instrument Shimadzu GCMS–QP5050A (column SPB-
5, 60000 × 0.25 mm), quadrupole mass analyzer,
electron impact, 70 eV, ion source temperature 190°С,
range of detected masses 34–650 Da.
1
chalcogenides 5 as proved by IR and Н, 13С NMR
spectra and the data of GC-MS analysis. The yield of
compound 5b was15%, of compound 5c, 18% with
respect to the i-Pr2S2 taken interaction and 34% with
respect to the reacted substrate.
Reactions of dichloroethenes (1a and 1b) with
diorganyldichalcogenides R2Y2. General procedure.
To a solution of potassium hydroxide in hydrazine
hydrate R2Y2 was added at stirring by portions or
dropwise in a quantity corresponding to the ratio R2Y2
–KOH 1 : 5. The mixture was stirred for 2 h at 80–85°
С, cooled to 25°С, and at constant stirring
dichloroethene 1а or 1b was added dropwise. After the
addition of the required amount of dichloroethene 1а
(1b) the mixture was stirred for 6 h. Reaction products
were extracted with ethyl ether (3 × 30–50 mL), the
extract was washed with water and dried with MgSO4.
Ether was distilled off, the residue was analyzed by
NMR, IR spectroscopy and GC-MS method. Then the
product was subjected to further treatment.
The identification of compounds 5, on the one
hand, confirms the assumed scheme of the process, and
on the other hand, has an independent practical
importance since ethynylsulfides 5 are used as key
reagents in the synthesis of versatile functionalized
organochalcogen compounds [19].
GC-MS method permitted the identification in the
reaction products compounds 7a–7d containing one
chlorine atom each (yield ~1–5%). The presence of
chlorine in compounds 7 when the reaction mixture
contains active nucleophiles RY‒ shows that the
chlorine atoms are linked to sp2-hybridized carbon. It is
presumable that compounds 7a–7d form by the addition
of nucleophiles RY‒ to chloroacetylene 4 (Scheme 3).
Compounds 3a and 3b (after recrystallization from
ethanol) and 3d were isolated in an individual state as
Z-isomers. Compounds 3c, 5b, and 5c were identified
Scheme 3.
_
H2O
_
4
+ RY
ClCH=CHYR
1
in the mixture by Н, 13С NMR, and mass spectra.
_OH
7a_7d
Compounds 7a–7d were identified only by GC-MS
method.
According to GC-MS data compounds 7a–7d
formed as a single isomer whose configuration we
failed to establish. Compound 7d formed in the least
yield (<1%) that may be due to the high reactivity of
PhSe‒ anion in the substitution of the chlorine in
chloroacetylene 4. At the same time PhS‒ anion being
the most active in addition reactions to the triple bond
sufficiently effectively reacted both along Scheme 2
and Scheme 3 (yield of compound 7а 5%). BnS‒ and
PrS‒ anions possess an intermediate reactivity, and the
yields of compounds 7b and 7c are ~3%.
{[(Z)-2-(Phenylsulfanyl)ethenyl]sulfanyl}benzene
(Z-3a). а. It was obtained from 5.46 g (0.025 mol) of
Ph2S2, 7.01 g (0.125 mol) of KOH, 30 mL of hydrazine
hydrate, and 2.42 g (0.025 mol) of 1,1-dichloroethene 1а.
Yield 76%. Light red fluid, bp 182–186°С (2 mmHg)
{Z-isomer, bp 170‒171°С (1 mmHg) [7]}. IR spec-
trum, ν, cm–1: 1583 (С=С). 1H NMR spectrum, δ, ppm:
6.49 s (2Н, СН=, J(HC12, C13H 8.1 Hz), 7.20–7.23 m
(2Н, Hp, C6H5), 7.28–7.32 m (4H, Hm, C6H5), 7.37–
7.39 m (4H, Ho, C6H5). 13С NMR spectrum, δ, ppm:
124.95 (СH=), 126.88 (Cp), 129.09 (Cm), 129.46 (Co),
135.18 (Ci). Mass spectrum: m/z: 244 [M]+. Found, %:
C 68.81; H 4.73; S 26.34. C14H12S2. Calculated, %: C
68.81; H 4.95; S 26.24. M 244.369.
Hence, the preparatively simple (25°С, available
reagents) reaction of dichloroethenes with organyl
dichalcogenides made it possible to prepare 1,2-
dichalcogenyl-substituted ethenes, and at optimization
of the reaction conditions, ethynylchalcogenides.
b. It was obtained from 5.13 g (0.0235 mol) of Ph2S2,
6.59 g (0.1175 mol) of KOH, 30 mL of hydrazine
hydrate, and 2.28 g (0.0235 mol) of 1,2-dichloroethene
1b. Yield 64%. Spectral characteristics are identical to
those reported above.
EXPERIMENTAL
IR spectra were recorded on a Bruker IFS-25 from
thin films, 1Н, 13С, and 77Se NMR spectra were registered
on a spectrometer Bruker DPX-400 (operating fre-
{[(E)-2-(Phenylsulfanyl)ethenyl]sulfanyl}benze-
ne (E-3a) was present as admixture (<1%) in crude
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 53 No. 8 2017

SYNTHESIS OF ORGANOCHALCOGEN COMPOUNDS PROCEEDING
1189
1
compound 3а. H NMR spectrum, δ, ppm: 6.52 s (2Н,
respect to reacted i-Pr2S2), yield of isomer Z-3c 7 and
13% respectively. IR spectrum, ν, cm–1: 1544 (С=С).
1H NMR spectrum, δ, ppm: 1.37 d (6Н, СН3), 3.15
septet (2Н, >СНS), 6.16 s (2Н, =СН). 13С NMR
spectrum, δ, ppm: 23.40 (CH3), 37.65 (>CHS), 122.30
(=CH). Mass spectrum: m/z 176 [M]+.
CH=). Mass spectrum: m/z 244 [M]+.
({[(Z)-2-(Benzylsulfanyl)ethenyl]sulfanyl}methyl)-
benzene (Z-3b). а. It was obtained from 3.0 g (0.012 mol)
of Bn2S2 in a solution of 3.42 g (0.06 mol) of KOH in
15 mL of hydrazine hydrate and 1.18 g (0.012 mol) of
1,1-dichloroethene 1а. Yield 1.97 g (59%), according
2-{[(E)-2-(Propan-2-ylsulfanyl)ethenyl]sulfanyl}-
1
1
to Н NMR spectrum it was a mixture of Z- and E-
propane (E-3с). H NMR spectrum, δ, ppm: 6.11 s
isomers, 10 : 1. At adding ethanol and cooling (‒18°С)
yellow crystals precipitated, mp 54–56°С, according to
1Н NMR data the crystals were pure Z-isomer 3b. IR
(2Н, =CH).
2-(Ethynylsulfanyl)propane (5с) was identified in
a mixture with compound 3с. Yield 34% with respect
to reacted i-Pr2S2. IR spectrum, ν, cm–1: 3293 (≡С–Н),
1
spectrum, ν, cm–1: 1545 (С=С). H NMR spectrum, δ,
ppm: 3.88 s (4H, СН2), 5.99 s (2H, =CH), 7.20–7.29 m
(10Н, Ph), satellite signals H–C13, 3J(HC12, C13H) 8.5 Hz.
13С NMR spectrum, δ, ppm: 38.07 (CH2), 123.07
(=CH), 127.22 (Cp), 128.55, 128.87 (Co, m), 137.63
(Ci). Mass spectrum: m/z 272 [M]+. Found, %: C
69.98; H 5.94; S 24.08. C16H16S2. Calculated, %: C
70.54; H 5.92; S 23.54. M 272.422.
1
2039 (C≡C). H NMR spectrum, δ, ppm: 2.85 s (1Н,
≡С–Н), the rest of the signals are overlapped with the
proton signals of compound 3с. 13С NMR spectrum, δ,
ppm: 23.52 (CH3), 39.23 (CH<), 65.78 (≡C–), 83.57
(≡C–H). Mass spectrum: m/z 100 [M]+.
{[(Z)-2-Phenylselenylethenyl]selenyl}benzene (Z-
3d). а. It was obtained from 3.12 g (0.01 mol) of
Ph2Se2, 2.81 g (0.05 mol) of KOH, 12 mL of hydrazine
hydrate, and 0.97 g (0.01mol) of 1,1-dichloroethene
1a. After extraction from the reaction mixture and
removal of the solvent we obtained 2.94 g (87%) of
yellow fluid, pure bisselenide 3d. IR spectrum, ν, cm–1:
b. It was obtained from 2.3 g (0.0093 mol) of Bn2S2,
2.62 g (0.047 mol) of KOН, 12 mL of hydrazine
hydrate, and 0.9 g (0.0093 mol) of 1,2-dichloroethene
1b. Yield 56%. Spectral characteristics are identical to
those reported above.
1
({[(E)-2-(Benzylsulfanyl)ethenyl]sulfanyl}methyl)-
1577 (С=С). H NMR spectrum, δ, ppm: 7.14 s (2H,
1
2
SeCH=, JSeH 11.6 Hz), 7.24–7.52 m (10H, Ph). 13С
benzene (E-3b). H NMR spectrum, δ, ppm: 3.93 s
(4H, СН2), 6.17 s (2H, =CH), 7.20–7.32 m (10Н, Ph). 13С
NMR spectrum, δ, ppm: 39.70 (CH2), 121.25 (=CH).
The 13С NMR signals of benzene rings coincide with
the same signals of the Z-isomer.
1
NMR spectrum, δ, ppm: 125.97 (CH=, JSe–C= 103.9,
2JSe–C=C 15.9 Hz). 77Se NMR spectrum, δ, ppm: 381.9.
Mass spectrum: m/z 340 [M]+.
{[(E)-2-Phenylselenylethenyl]selenyl}benzene (E-
3d) was detected only by GC-MS method. Mass
spectrum: m/z 340 [M]+.
Ethynylsulfanylmethylbenzene (5b) was identified
in the mixture at the isolation of unpurified compound
3b. Yield 15%. IR spectrum, ν, cm–1: 3285 (≡С–Н). 1H
NMR spectrum, δ, ppm: 2.79 s (1Н, ≡С–Н), 4.01 s
(2Н, CH2), 7.21–7.33 m (5Н, Ph). 13С NMR spectrum,
δ, ppm: 64.0 (≡С–), 83.36 (≡С–Н), the other signals
are overlapped with signals of compound 3b. Mass
spectrum: m/z 148 [M]+.
Compounds 7a–7d were identified only by GC-MS
method. The m/z value of the molecular ion is given
only for isotopes 35Cl, 37Cl (their intensity ratio
corresponds to the presence of a single chlorine in the
molecule).
2-{[(Z)-2-(Propan-2-ylsulfanyl)ethenyl]sulfanyl}-
propane (Z-3с) was obtained from 2.15 g (0.0143 mol)
of i-Pr2S2, 4.01 g (0.0715 mol) of KOН, 18 mL of
hydrazine hydrate, and 2.77 g (0.0286 mol) 1,1-dichlo-
(2-Chloroethenyl)sulfanylbenzene (7a). Mass
spectrum: m/z 172, 170 [M]+.
[(2-Chloroethenyl)sulfanyl]methylbenzene (7b).
Mass spectrum: m/z 186, 184 [M]+.
1
roethene 1a. According to Н NMR spectrum it was a
mixture of the initial i-Pr2S2, 2-(ethynylsulfanyl)
propane 5с, and compound 3с (mixture of Z- and E-
isomers, 5 : 1) in a ratio 5.0 : 2.4 : 1. Conversion of i-
Pr2S2 52%. Yield of compound 3с (isomers mixture)
was 8% (with respect to taken i-Pr2S2) and 16% (with
2-(2-Chloroethenylsulfanyl)propane (7с). Mass
spectrum: m/z 138, 136 [M]+.
(2-Chloroethenyl)selanylbenzene (7d). Mass
spectrum: m/z 220, 218 (80Se) [M]+.
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LEVANOVA et al.
9. Beletskaya, I.P. and Ananikov, V.P., Eur. J. Org.
1190
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