N,S-substituted dienes from mono (arylthio) substituted- and S-, S,S-substituted dienes

Article abstract of DOI:10.1080/10426500214874

Mono(thio)substituted dienes 1a-1b gave compounds 3a-c and 5d-g with piperazine and piperidine derivatives in dichloromethane. Compounds 8, 9, and 10 were obtained from the reactions of perchlorobutadiene (6) with 1,4-butanedithiol (7) in ethanol in the presence of sodium hydroxide. Compounds 12a-b, 13a-b were obtained from the reactions of perchlorobutadiene (6) with allylmercaptan (CH₂=CH-CH₂-SH) and mercaptoethanol (HO-CH₂-CH₂-SH).

Full text of DOI:10.1080/10426500214874

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N,S-Substituted Dienes from Mono(arylthio)substituted-
and S-, S,S-Substituted Dienes
a
Cemil İbiş , Zeliha Gökmen a & Nihal Yilmaz Bozkurt a
a Istanbul University , Avcılar-Istanbul, Turkey
Published online: 27 Oct 2010.
To cite this article: Cemil İbiş , Zeliha Gökmen & Nihal Yilmaz Bozkurt (2002) N,S-Substituted Dienes from
Mono(arylthio)substituted- and S-, S,S-Substituted Dienes, Phosphorus, Sulfur, and Silicon and the Related Elements, 177:12,
2907-2914, DOI: 10.1080/10426500214874
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Phosphorus, Sulfur and Silicon, 2002, Vol. 177:2907–2914
C
Copyright 2002 Taylor & Francis
1042-6507/02 $12.00 + .00
DOI: 10.1080/10426500290146956
N,S-SUBSTITUTED DIENES FROM
MONO(ARYLTHIO)SUBSTITUTED- AND
S-, S,S-SUBSTITUTED DIENES
˙
Cemil Ibis¸, Zeliha Go¨kmen, and Nihal Yilmaz Bozkurt
Istanbul University, Avcılar-Istanbul, Turkey
(Received March 26, 2002)
Mono(thio)substituted dienes 1a–1b gave compounds 3a–c and 5d–g
with piperazine and piperidine derivatives in dichloromethane. Com-
pounds 8, 9, and 10 were obtained from the reactions of perchlorobuta-
diene (6) with 1,4-butanedithiol (7) in ethanol in the presence of sodium
hydroxide. Compounds 12a–b, 13a–b were obtained from the reactions
of perchlorobutadiene (6) with allylmercaptan (CH2 CH CH2 SH)
and mercaptoethanol (HO CH2 CH2 SH).
Keywords: Disulphid; dithiol; hexachlorobutadiene; mono- and
disubstituted halodienes; mono(thio)substituted nitrodiene; N,S-
thiosubstituted nitrodiene; piperazine; piperidine; thioether; thiol
The reactions of nitrodiene compounds with some thiols and amines are
8
known.1 Previously, we have obtained N,S-substituted dienes from
the reaction of mono(aryl- and alkylthio) substituted dienes with some
11
amines (primary amine, piperazine, and piperidine, etc.).9
The reactions of perchlorobutadiene with thiols in DMF, DMSO, and
20
EtOH have been reported previously.12
Thiosubstituted halodienes
were obtained from the reactions of perchlorobutadiene with methane
thiol in EtOH.21
The aim of this study was to synthesize new S-, S,S- and N,S-
substituted 1,3-diene compounds and to determine their structures.
The piperazine compounds are important for therapeutical use, also
some piperazine compounds were used in gen transfer reactions.22,23
The piperidinyl derivatives show an excellent biological activity.24
We thank the Research Fund of the University of Istanbul for financial support of this
work.
˙
Address correspondence to Cemil Ibis¸, Istanbul University, Engineering Faculty, De-
partment of Chemistry, Avcilar-Istanbul, Turkey.
2907

˙
C. Ibis¸ et al.
2908
The occurence of sulphur as a donor atom for transition metals is
a well-known phenomenon. It acts as a very good ligating atom when
in the form of the sulfide ion (S2 ) or as a mercaptide ion (RS ), but
complexes of sulphur as a thioether (RSR) are much less abundant.25
Compounds 1a26 and 1b27 gave new compounds 3a–c with piperazine
derivatives. Compounds 5d, 5e, 5f, and 5g were obtained from the reac-
tions of compounds 1a and 1b with piperidine derivatives (Scheme 1).
The obtained products are yellow and stable crystals.
SCHEME 1
The novel compounds 8, 9, and 10 were obtained from the reaction of
perchlorobutadiene with 1,4-butanedithiol. Compound 8 is a thioether,
compound 9 is a disulphids, compound 10 is an interesting compound
1
with a cyclic structure. The H-NMR spectrum of compound 10 shows
multiplet signals at = 1.6–2.2 and 2.4–3.4 ppm for the protons of the
CH2 groups.
Perchlorobutadiene (6) gave new unknown 12a–b and 13a–b com-
pounds with allylthiol and 2-mercaptoethanol in EtOH in the presence
of NaOH (Scheme 2).
The 1H-NMR spectra of 12a–b and 13a–b showed the expected sig-
nals. These products are viscouse oil and stable compounds. The struc-
tures of S-, S,S-, and N,S-substituted diene compounds were determined
by microanalysis and spectroscopic data.

N,S-Substituted Dienes from Mono(arylthio)- and S-, S,S-Substituted Dienes 2909
SCHEME 2
EXPERIMENTAL SECTION
r 1H-NMR: Bruker AC 200 L.
r
IR: Shimadzu FTIR-8101.
Microanalyses: Carlo-Erba 1106 Elemental Analyser.
UV: HP 8453.
Melting Points: Bu¨chi SMP 20.
Products were isolated by column chromatography on silica gel (Fluka
Kieselgel 60, particle size 63–200 m).
TLC plates silica 60 F254 (Merck, Darmstadt), detection with ultravi-
olet light (254 nm).
r
r
r
r
r
Preparation of S-Substituted Polyhalonitrodienes
General Procedure I
Equimolar amounts of 1,1,3,4,4-pentachloro-2-nitro-1,3-butadiene in
10 ml of ethanol and thiols in 10 ml ethanol were mixed and NaOH (in
8 ml of water) was added at room temperature. The mixture was stirred
for 24 h. Chloroform was added to the reaction mixture. The organic
layer was separated and washed with water (4 30 ml), and dried with

˙
C. Ibis¸ et al.
2910
MgSO4. The solvent was evaporated and the residue was purified by
column chromatography on silica gel.
Preparation of N,S-Substituted Polyhalonitrodienes
General Procedure II
Equimolar amounts of S-substituted polyhalonitrodienes and piper-
azine or piperidine derivatives were stirred in dichloromethane until
completion of the reaction (TLC). Chloroform was added to the reac-
tion mixture. The organic layer was separated and washed with water
(4 30 ml), and dried with MgSO4. The solvent was evaporated and
the residue was purified by column chromatography on silica gel.
1,3,4,4-Tetrachloro-mono(p-methylphenylthio)-2-nitro-1,3-butadiene
(1a). Compound 1a was synthesized from 1,1,3,4,4-pentachloro-2-
nitro-1,3-butadiene (2 g, 7.37 mmol) and p-methylphenylthiol (0.92 g,
7.37 mmol) according to the general procedure I. The mixture was
purified by column chromatography with carbon tetrachloride as
eluent.
1a: Yield: 2.4 g (90%); m.p. 112–113 C. UV (chloroform):
344 nm.
= 234,
max
1,3,4,4-Tetrachloro-mono(p-chlorophenylthio)-2-nitro-1,3-butadiene
(1b). Compound 1b was synthesized from 1,1,3,4,4-pentachloro-2-
nitro-1,3-butadiene (2 g, 7.37 mmol) and p-chlorophenylthiol (1 g,
7.37 mmol) according to the general procedure I. The mixture was
purified by column chromatography with carbon tetrachlorid as eluent.
1b: Yield: 2.2 g (79%); m.p. 113–115 C. UV (chloroform):
339 nm.
= 245,
max
3,4,4-Trichloro-1-(4-fluorophenylpiperazine)-1-(p-methylphenylthio)-
2-nitro-1,3-butadiene (3a). Compound 3a was synthesized from 1,3,4,4-
tetrachloro-1-(p-methylphenylthio)-2-nitro-1,3-butadiene (0.119 g, 0.33
mmol) and 4-(p-fluorophenyl)piperazine (0.059 g, 0.33 mmol) according
to the general procedure II. The mixture was purified by crystallization
in methanol.
3a: Yield: 0.12 g (73%); m.p. 156–157 C. Rf = 0.6923 (CHCl3/
Petroleumether 2:1). IR (KBr): = 2980, 3010 cm 1 (C H), 1600 (C C),
1290, 1520 (C NO2). 1H NMR (CDCl3):
8 Ar H), 2.8–3.1, 3.6–3.9 (m, 8H, 4CH2), 2.4 (m, 3H, CH3). UV (chloro-
form): max = 230, 388 nm. C21H19Cl3N3O2SF (502.825): calcd. C, 50.16;
H, 3.80; N, 8.35; found C, 50.50; H, 3.63; N, 8.23. MS: 503.
= 6.9–7.5 ppm (m, 8H,
3,4,4-Trichloro-1-(p-methylphenylthio)-1-(N-phenylpiperazine)-2-nitro-
1,3-butadiene (3b). Compound 3b was synthesized from 1,3,4,
4-tetrachloro-1-(p-methylphenylthio)-2-nitro-1,3-butadiene (0.12 g,

N,S-Substituted Dienes from Mono(arylthio)- and S-, S,S-Substituted Dienes 2911
0.33 mmol) and N-phenylpiperazine (0.054 g, 0.33 mmol) according to
the general procedure II. The mixture was purified by crystallization
in methanol.
3b: Yield: 0.123 g (76%); m.p. 178–179 C. Rf = 0.3947 (CHCl3/
Petroleumether 2:1). IR (KBr): = 2970, 3000 cm 1 (C H), 1600 (C C),
1230, 1510 (C NO2). 1H NMR (CDCl3): = 6.8–7.4 ppm (m, 9H, Ar H),
2.6–3.1, 3.4–4.0 (m, 8H, 4CH2), 2.4 (m, 3H, CH3). UV (chloroform):
= 233, 387 nm. C21H20Cl3N3O2S (484.835): calcd. C, 52.02; H,
max
4.15; N, 8.66; found C, 52.07; H, 3.99; N, 8.51.
3,4,4-Trichloro-1-(p-chlorophenylthio)-1-(4-fluorophenylpiperazine)-
2-nitro-1,3-butadiene (3c). Compound 3c was synthesized from
1,3,4,4-tetrachloro-1-(p-chlorophenylthio)-2-nitro-1,3-butadiene (0.1 g,
0.26 mmol) and 4-(p-fluorophenyl)piperazine (0.047 g, 0.26 mmol)
according to the general procedure II. The mixture was purified by
crystallization in methanol.
3c: Yield: 0.095 g (70%); m.p. 179–180 C. Rf = 0.6428 (CHCl3/
Petroleumether 2:1). IR (KBr): = 2980, 3010 cm 1 (C H), 1580 (C C),
1280, 1500 (C NO2). 1H NMR (CDCl3):
8 Ar H), 2.8–3.2, 3.4–3.95 (m, 8H, 4CH2). UV (chloroform): max = 251,
385 nm. C20H16Cl4N3O2SF (523.294): calcd. C, 45.91; H, 3.08; N, 8.03;
found C, 45.92; H, 3.02; N, 7.93.
= 6.7–7.5 ppm (m, 8H,
3,4,4-Trichloro-1-(p-methylphenylthio)-1-(4-methylpiperidino)-2-nitro-
1,3-butadiene (5d). Compound 5d was synthesized from 1,3,4,4-
tetrachloro-1-(p-methylphenylthio)-2-nitro-1,3-butadiene (0.2 g, 0.55
mmol) and 4-methylpiperidine (0.055 g, 0.55 mmol) according to the
general procedure II. The mixture was purified by crystallization in
methanol.
5d: Yield: 0.212 g (92%); m.p. 149–150 C. Rf = 0.4375 (CHCl3/
Petroleumether 1:1). IR (KBr): = 2890, 2900 cm 1 (C H), 1600 (C C),
1290, 1550 (C NO2). 1H NMR (CDCl3): = 7.2–7.5 ppm (m, 4H, Ar H),
3.5–4.1 (m, H, CH), 3.4–3.1 (m, 4H, 2CH2), 1.4–1.8 (m, 4H, 2CH2), 2.4
(m, 3H, S CH3), 0.5–0.9 (m, 3H, CH3). UV (chloroform):
390 nm. C17H19Cl3N2O2S (421.776): calcd. C, 48.41; H, 4.54; N, 6.64; S
7.60; found C, 48.13; H, 4.20; N, 6.39; S, 7.50.
= 240,
max
3,4,4-Trichloro-1-(4-benzylpiperidino)-1-(p-methylphenylthio)-2-nitro-
1,3-butadiene (5e). Compound 5e was synthesized from 1,3,4,4-
tetrachloro-1-(p-methylphenylthio)-2-nitro-1,3-butadiene (0.2 g, 0.55
mmol) and 4-benzylpiperidine (0.097 g, 0.55 mmol) according to the
general procedure II. The mixture was purified by crystallization in
methanol.

˙
C. Ibis¸ et al.
2912
5e: Yield: 0.145 g (52%); m.p. 122–123 C. Rf = 0.6310 (CHCl3/
Petroleumether 1:1). IR (KBr): = 2970, 3000 cm 1 (C H), 1525 (C C),
1240, 1510 (C NO2). 1H NMR (CDCl3): = 6.9–7.5 ppm (m, 9H, Ar H),
3.2–4.1 (m, H, CH), 3.0–3.3 (m, 4H, 2CH2), 1.4–1.9 (m, 4H, 2CH2), 2.2–
2.3 (m, 2H, CH2), 2.4 (m, 3H, S CH3). UV (chloroform): max = 231, 390
nm. C23H23Cl3N2O2S (497.844): calcd. C, 55.49; H, 4.65; N, 5.62; S 6.44;
found C, 55.20; H, 4.35; N, 5.37; S, 6.13.
3,4,4-Trichloro-1-(p-chlorophenylthio)-1-(4-methylpiperidino)-2-nitro-
1,3-butadiene (5f). Compound 5f was synthesized from 1,3,4,4-
tetrachloro-1-(p-chlorophenylthio)-2-nitro-1,3-butadiene (0.2 g, 0.52
mmol) and 4-methylpiperidine (0.052 g, 0.55 mmol) according to the
general procedure II. The mixture was purified by crystallization in
methanol.
5f: Yield: 0.153 g (66%); m.p. 172–173 C. Rf = 0.7330 (CHCl3/
1
Petroleumether 1:1). IR (KBr):
= 2970, 2985 cm (C H), 1580,
1
1600 (C C), 1290, 1545 (C NO2). H NMR (CDCl3): = 7.3–7.5 ppm
(m, 4H, Ar H), 3.5–4.1 (m, H, CH), 3.1–3.4 (m, 4H, 2CH2), 1.5–1.8 (m,
4H, 2CH2), 0.6–1.1 (m, 3H, CH3). UV (chloroform): max = 253, 389 nm.
C16H16Cl4N2O2S (442.194): calcd. C, 43.40; H, 3.65; N, 6.33; S 7.25;
found C, 43.09; H, 3.32; N, 6.22; S, 6.91.
3,4,4-Trichloro-1-(4-benzylpiperidino)-1-(p-chlorophenylthio)-2-nitro-
1,3-butadiene (5g). Compound 5g was synthesized from 1,3,4,4-
tetrachloro-1-(p-chlorophenylthio)-2-nitro-1,3-butadiene (0.2 g, 0.52
mmol) and 4-benzylpiperidine (0.092 g, 0.52 mmol) according to the
general procedure II. The mixture was purified by crystallization in
methanol.
5g: Yield: 0.147 g (54%); m.p. 129–130 C. Rf = 0.40 (CHCl3/
Petroleumether 1:1). IR (KBr): = 2980, 3000 cm 1 (C H), 1585 (C C),
1290, 1520 (C NO2). 1H NMR (CDCl3): = 6.9–7.5 ppm (m, 9H, Ar H),
3.4–4.2 (m, H, CH), 3.0–3.3 (m, 4H, 2CH2), 1.4–2.0 (m, 4H, 2CH2),
2.3–2.5 (m, 2H, CH2). UV (chloroform):
C22H20Cl4N2O2S (513.292): calcd. C, 50.98; H, 3.88; N, 5.40; S 6.18;
found C, 50.68; H, 3.51; N, 5.10; S, 5.92.
= 250, 389 nm.
max
1,2,3,4,4-Pentachloro-1-(2-hydroxyethylthio)-1,3-butadiene (12b).
Compound 12b was synthesized from 1,1,2,3,4,4-hexachloro-1,3-
butadiene (4 g, 15.32 mmol) and 2-mercaptoethanol (2.394 g,
30.64 mmol) according to the general procedure I. The mixture was pu-
rified by column chromatography with petroleumether and chloroform
as eluent.
12b: Yield: 1.8 g (76%); oil. Rf = 0.48 (CHCl3). IR (film): = 2970,
1
2990 cm (C H), 1550, 1600 (C C), 3480 (OH). 1H NMR (CDCl3):

N,S-Substituted Dienes from Mono(arylthio)- and S-, S,S-Substituted Dienes 2913
= 3.6–3.9 ppm (m, 2H, OH CH2), 2.6–3.1 (m, 2H, S CH2). C6H5Cl5SO
(302.435): calcd. C, 23.82; H, 1.66; found C, 24.75; H, 1.77. MS: 302.
1,4-Bis(2-hydroxyethylthio)-1,2,3,4-tetrachloro-1,3-butadiene (13b).
Compound 13b was synthesized from 1,1,2,3,4,4-hexachloro-1,3-
butadiene (4 g, 15.32 mmol) and 2-mercaptoethanol (7.18 g, 91.89 mmol)
according to the general procedure I. The mixture was purified by
column chromatography with ethylacetate and petroleumether as
eluent.
13b: Yield: 1.373
g
(26%); oil. Rf
=
0.3333 (ethylacetate/
1
petroleumether 1:1). IR (film): = 2970, 2985 cm (C H), 1530, 1620
(C C), 3490 (OH). C8H10Cl4S2O2 (344.103): calcd. C, 27.92; H, 2.92;
found C, 27.82; H, 3.01.
1-Mono-(allylthio)-1,2,3,4,4-pentachloro-1,3-butadiene (12a), 1,4-
bis-(allylthio)-1,2,3,4-tetrachloro-1,3-butadiene (13a). Compounds 12a
and 13a were synthesized from 1,1,2,3,4,4-hexachloro-1,3-butadiene
(2 g, 7.66 mmol) and allylmercaptan (0.57 g, 7.66 mmol) according to the
general procedure I. The mixture was purified by column chromatogra-
phy with petroleumether as eluent. Column chromatography gave the
compounds 12a, 13a as oils.
12a: Yield: 1.5 g (68%); oil. Rf = 0.7142 (petroleumether). IR (film):
1
1
2900, 3000 cm (C H), 1550 (C C), 655 (C Cl). H NMR (CDCl3):
= 5.7–6.1 ppm (m, H, CH ), 5.0–5.5 (m, 2H, CH2 ), 3.3–4.9 (m, 2H,
CH2). C7H5Cl5S (298.447): calcd. C, 28.17; H, 1.68; S, 10.74; found C,
28.36; H, 1.39; S, 11.02.
13a: Yield: 0.5 g (20%); oil. Rf = 0.2381 (petroleumether). IR (film):
1
1
= 2900, 3020 cm (C H), 1550, 1610 (C C), 650 (C Cl). H NMR
(CDCl3): = 5.6–6.1 ppm (m, 2H, 2CH ), 4.9–5.4 (m, 4H, 2CH2 ), 2.4–
3.6 (m, 4H, 2CH2). C10H10Cl4S2 (336.132): calcd. C, 35.73; H, 2.99; S,
19.07; found C, 36.04; H, 2.99; S, 19.41.
4,40-Butanedithio-bis(1,1,2,3,4-pentachloro-1,3-butadiene) (8), 1,6,7,
12-tetrathio-bis-(1,2,3,4,4-pentachloro-1,3-butadienyl)-icosan (9), 2,3,
4,5-tetrachloro-1,6-dithia-cyclodeca-2,4-dien (10). Compounds 8, 9,
and 10 were synthesized from 1,1,2,3,4,4-hexachloro-1,3-butadiene
(2 g, 7.66 mmol) and butandithiol (0.935 g, 7.66 mmol) according to
the general procedure I. The mixtures were purified by column chro-
matography with petroleumether as eluent. Column chromatography
gave the compounds 8, 9, and 10.
8: Yield: 0.6 g (14%); m.p: 77–78 C. Rf = 0.7659 (petroleumether).
1
IR (film): = 2850, 2950 cm (C H), 1550, 1600 (C C). 1H NMR
(CDCl3): = 1.6–2.0 ppm (m, 4H, CH2 CH2), 2.8–3.2 (m, 4H, 2CH2S).
C12H8Cl10S2 (570.856): calcd. C, 25.25; H, 1.41; S, 11.23; found C, 25.22;
H, 1.19; S, 10.98.

˙
C. Ibis¸ et al.
2914
9: Yield: 0.01 g (1%); oil. Rf = 0.5500 (petroleumether). IR (film):
= 2860, 2980, 3000 cm 1 (C H), 1550, 1600 (C C). 1H NMR (CDCl3):
= 1.6–2.2 ppm (m, 8H, 4CH2), 2.8–3.2 (m, 8H, 4CH2S). C16H16Cl10S4
(691.092): calcd. C, 27.80; H, 2.33; S, 18.56; found C, 27.53; H,1.99; S,
18.37.
10: Yield: 0.05 g (2%); oil. Rf = 0.4500 (petroleumether). IR (film):
1
1
= 2930, 2860 cm (C H), 1550, 1600 (C C). H NMR (CDCl3):
=
1.6–2.2 ppm (m, 4H, 2CH2), 2.4–3.4 (m, 4H, 2CH2S). C8H8Cl14S2
(310.093): calcd. C, 3099; H, 2.60; S, 20.68; found C, 30.68; H, 2.40;
S, 20.41.
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