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Direct synthesis of disulfides from alkyl halides using thiourea and CCl4 in
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DOI: 10.1007/s13738-015-0610-3

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Direct synthesis of disulfides from alkyl
halides using thiourea and CCl4 in glycerol

Mohammad Abbasi & Dariush Khalili

Journal of the Iranian Chemical

Society

ISSN 1735-207X

J IRAN CHEM SOC

DOI 10.1007/s13738-015-0610-3

1 23
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J IRAN CHEM SOC
DOI 10.1007/s13738-015-0610-3
ORIGINAL PAPER
Direct synthesis of disulfides from alkyl halides using thiourea
and CCl4 in glycerol
Mohammad Abbasi · Dariush Khalili 
Received: 28 October 2014 / Accepted: 10 February 2015
© Iranian Chemical Society 2015
Abstract  Dialkyl disulfides were obtained on the basis of
the reaction of alkyl halides and thiourea in the presence
of CCl4 and Et3N. This procedure enables the odorless and
one-pot synthesis of disulfides by employing cheap, easy-
to-handle and readily available reagents and substrates in
wet glycerol.
Graphical abstract  ous oxidants. A number of reagents and metal-based cata-
Keywords  Disulfide · Odorless · Alkyl halide · Thiourea
Introduction
The disulfide motif (disulfanes) is exemplified as an impor-
tant subunit in industrial and pharmaceutical products
[1–4]. Disulfides are acceptable precursors for the prepa-
ration of self-assembled monolayers and monolayer-pro-
tected clusters [5, 6]. These compounds are also recognized
M. Abbasi 
Department of Chemistry, Faculty of Sciences, Persian Gulf
University, 75169 Bushehr, Iran
D. Khalili (*) 
Department of Chemistry, College of Sciences, Shiraz University,
71454 Shiraz, Iran
e-mail: d_kh59@yahoo.com; khalili@shirazu.ac.ir
as key intermediates with many applications in synthetic
organic chemistry [7–12]. Since disulfide functionality is
much less reactive and more stable toward reagents and
functional groups than thiol group, the disulfides are used
as protected thiols in organic synthesis [13–15]. Gener-
ally, the common pathway for the synthesis of symmetric
disulfides involves oxidation reaction of thiols with vari-
lysts such as 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-
hexachloride [16], activated carbon–air system [17],
PhSeZnCl [18], supported iron oxide nanoparticles [19],
K+/CH3CN/O2 [20], bipyridinum hydrobromide perbro-
mide [21], (NH4)6Mo7O24.4H2O/KBrO3 [22], hexameth-
ylenetetramine–bromine complex [23], sulfonyl chloride
[24] and other oxidizing agents [25–29] have been exam-
ined to promote the oxidation of thiols to disulfides under
controlled conditions. Disulfides can also be prepared from
alcohols [30] and organic thiocyanates [31, 32] as alterna-
tive methods. However, these reported methods (thiol as a
substrate) require foul-smelling thiols. To solve this impor-
tant problem, researches are focusing on the development
of new alternative substrates such as alkyl halides instead
of thiols [33–38]. It is worthy to note that alkyl halides can
be converted into the disulfides in the presence of sulfur
sources or sulfur transfer reagents with different mecha-
nism. The sulfur transfer reagents including disulfide dian-
ion [39], tetrathiomolybdate complex [40], borohydride/
sulfur [41] and sulfur element in strong alkaline media
[42]. In addition, oxidation of the in situ-generated thiols
from alkyl halides using sulfur sources can be one of the
attractive approaches to disulfides in view of the fact that
alkyl halides, compared with the thiols, are more commer-
cially available and odorless. Recently, we documented the
oxidation of in situ-generated thiols from the reaction of
alkyl halides with thiourea in the presence of MnO2 [43,
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44] and elemental sulfur [45] which provides a new direc- Table 1  Optimization of the reaction conditions
tion for the one-pot synthesis of disulfides (disulfanes).
Due to the high oxidation capability of thiourea [46] and
thiol overoxidation in alkaline conditions, proper choice of
the oxidant can be an important factor. The reaction of thi-
ols with CCl4, in the presence of a base, is a possible and
Entry Base Solvent Yield (%)a
straightforward method for the mild oxidation of the thiols
into the corresponding disulfides [47]. We now describe the 1 NaHCO3 Wet glycerol 26
development of an odorless disulfide synthesis from alkyl 2 Na2CO3 Wet glycerol 44
halides using thiourea and CCl4 in basic media. 3 K2CO3 Wet glycerol 61
4 Na3PO4 Wet glycerol 67
5 DBU Wet glycerol 72
Results and discussion 6 Et3N Wet glycerol 90
7b Et3N Glycerol 45
In the preliminary experiment, we used benzyl chloride 1a 8 Et3N H 2O 76
(2 mmol), thiourea (2.5 mmol) and CCl4 (2 mmol) as start- 9 Et3N CHCl3 40
ing materials and different bases (3.5 mmol) in glycerol as 10 Et3N CH3CN 89
an inexpensive media at 50 °C (Table 1). Dibenzyl disulfide 11 Et3N EtOAc 11
2a was obtained in 26 % yield, when NaHCO3 was used 12 – Glycerol 0
as base (entry 1). Then several inorganic and organic bases 13 Et3N None 17
were screened under the same reaction conditions. Among
common bases, Et3N proved to be most effective (entry Reaction conditions: R–X (2 mmol), thiourea (2.5 mmol), base
(3.5 mmol), CCl4 (2 mmol), solvent (2 mL), 50 °C, 12 h
6), while Na2CO3, K2CO3 and Na3PO4 gave slightly lower
a
rates and yields (Table 1, entries 2–4).   Isolated yields
b
Organic bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene   Without addition of 0.1 mL of H2O
(DBU) led to even slower reaction (Table 1, entry 5). In the
presence of such bases (except Et3N), a mixture of benzyl (entry 1), 4-methylbenzyl chloride 1b (entry 2), benzyl bro-
sulfide and benzyl disulfide was obtained. We then examined mide 1c (entry 3) and 4-bromo benzyl bromide 1d (entry 4)
the effect of different solvents, such as H2O, CHCl3, CH3CN, readily reacted in excellent yields (88–97 %) under the reac-
EtOAc and glycerol (Table 1, entries 6–12). Among the sol- tion conditions to give the corresponding disulfides 2a–c.
vents, the best results were obtained with the wet glycerol Also, allylic substrates 1e and 1f were, respectively, con-
and afforded satisfying yield (90 %, entry 6). It is notewor- verted to 2d and 2e disulfides in excellent yields (Table 2,
thy that for successful transformation of alkyl halides to entries 5 and 6). Moreover, primary alkyl bromides and
disulfides a few drops (0.1 mL) of water should be added to iodides (entries 7–11) were efficiently converted into the
the reaction mixture (comparison with entry 7). When the corresponding disulfides 2f–j in good to high yields. A
model reaction was run in the absence of 0.1 mL of water, range of acyclic and cyclic secondary alkyl halides also
the corresponding disulfide (2a) was produced in 59 % yield. underwent this transformation efficiently. The reaction of
The yield of disulfide 2a when using H2O as solvents was secondary halides (entries 12–14) with thiourea proceeded
76 % (entry 8). The reaction efficiency was low in halogen- sluggishly and remained incomplete after 12 h. However,
ated solvent such as chloroform (entry 9). The reaction could these halides such as 2-bromo propane 1 l, 2-bromo butane
perform in high yield in CH3CN (entries 10). Using ethyl 1 m and cyclohexyl bromide 1n had been completely con-
acetate as solvent, however, gave 11 % of the desired benzyl sumed during 24 h and the corresponding disulfides were
disulfide (entry 11). However, disulfide formation was not produced in good to excellent yields. To show the value of
observed in the absence of base indicating that type of base the present work, we compared the results of our method
(here Et3N) is crucial for the reaction (Table 1, entry 12). with some other reported results in the literature for the
Also, when the reaction was conducted without solvent, the preparation of benzyl disulfide 2a from benzyl chloride as a
amount of oxidized product 2a was decreased (Table 1, entry starting substrate (Table 3). These comparative results estab-
13). After achieving the optimized reaction conditions, the lish that present system is an effective method (for the syn-
scope of alkyl halides was explored (Table 2). thesis of disulfides) with respect to yield and reaction condi-
Alkyl halides including benzylic, allylic, primary and tion over the existing methods.
secondary halides all participated in this reaction smoothly On the basis of the previous reports [42], a plausible
to afford the expected disulfides at 50 °C in good to excel- mechanism to rationalize this transformation is illustrated
lent yields. Benzylic substrates such as benzyl chloride 1a in Scheme 1.

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Table 2  Conversion of various alkyl halides (1) into disulfides (2)

Entry R–X RS–SR Yield (%)a References

1 1a 2a 90 [39]

2 1b 2b 88 [43]

3 1c 2a 95 [39]

4 1d 2c 97 [43]

5 1e 2d 91 [43]

6 1f 2e 94 [41]

7 1 g 2f 84 [48]

8 1 h 2 g 81 [22]

9 1i 2 h 83 [43]

10 1j 2i 88 [45]

11 1 k 2j 86 [43]

12b 1 l 2 k 75 [45]

13b 1 m 2 l 86 [19]

14b 1n 2 m 87 [43, 44]

Reaction conditions: R–X (2 mmol), thiourea (2.5 mmol), Et3N (3.5 mmol), CCl4 (2 mmol), wet glycerol (2 mL glycerol + 0.1 mL H2O), 50 °C, 12 h
a
  Isolated yields
b
  The reaction was conducted for 24 h

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Table 3  Comparison results of our method with other reported systems for the preparation of benzyl disulfide 2a from benzyl chloride
Entry System, condition Time (h) Yield (%) References

1 Thiourea, CCl4, Et3N, 50 °C, glycerol 12 90 This work

2 [(C6H5CH2N(Et)3)6Mo7S24] 24 54 [40]
3 Thioacetamide, CuCl, DMF, 110 °C 5 70 [29]
4 Thiourea, MnO2, PEG, 35 °C 4 86 [43]
5 Thiourea,S8, PEG, 40 °C 3 91 [45]
6 Na2S, Didecyl dimethyl-ammonium bromide, S8, H2O + CHCl3, 50–25 °C 4 88 [39]
7 CuCl/potassium 5-methyl-1,3,4-oxadiazole-2-thiolate, DMF, 130 °C 0.5 86 [38]

Scheme 1  Proposed reaction mechanism

Based on this proposed mechanism, the S-alkylisothi- Experimental

ouronium salt is formed by the nucleophilic substitution
of an alkyl halide with thiourea. Subsequently, hydrolysis
of S-alkylisothiouronium salt smoothly occurs in alkaline
media to produce thiol moiety which undergoes oxidation
by CCl4 to afford the disulfide product. To find support-
ing evidence for the mechanism of the reaction, a reac-
tion was performed on a large scale using benzyl chloride
(20 mmol), thiourea (25 mmol) and CCl4 (20 mmol) as
starting materials in the presence of Et3N (35 mmol) under
optimized reaction conditions. After 12 h, the reaction mix-
ture was distilled off. The collected distillate was washed
with HCl (1.5 M) solution and dried over anhydrous
Na2SO4. 1H-NMR of this distillate in d6-DMSO showed
the presence of the CHCl3 proton at 7.30 and a peak at
77.3 ppm in 13C-NMR, which are indicative of the forma-
tion of chloroform as a by-product.
General
Chemicals were either purchased from Fluka, Merck, and
Aldrich Chemical Companies or were prepared in our lab-
oratories. Most of the products were purified by column
chromatography or recrystallization from appropriate sol-
vents and were identified by 1H NMR, 13C NMR and ele-
mental analyses. Progress of the reactions was monitored
by TLC using silica gel polygrams SIL G/UV 254 plates.
NMR spectra were recorded on a Bruker Avance DPX
250 MHz Instrument in CDCl3 solvent using TMS as inter-
nal standard. Chemical shifts were reported in ppm (δ), and
coupling constants (J), in Hertz. Elemental analyses were
determined in our department using ThermoFinnigan Flash
EA 1112 Series.

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General procedure
A mixture of an alkyl halide (2 mmol), thiourea (2.5 mmol),
Et3N (3.5 mmol) and CCl4 (2 mmol) in wet glycerol (2 mL
glycerol + 0.1 mL H2O) was stirred magnetically at 50 °C
for 12–24 h. Then H2O (1 mL) was added to the reac-
tion mixture and the reaction was extracted with EtOAc
(3 × 2 mL). The organic layers were decanted, combined,
dried over Na2SO4, and concentrated to yield the crude
disulfide, which was further purified by silica gel chroma-
tography using low-boiling petroleum ether as eluent to
provide the desired disulfides in good to excellent yields
(Table 2).
Bis(4-methylbenzyl) disulfide (2b) colorless oil; 1HNMR
(250 MHz, CDCl3): δ  = 2.21 (s, 6H), 3.71 (s, 4H), 7.05–
7.33 (m, 8H); 13CNMR (62.5 MHz, CDCl3): δ  = 137.6,
134.8, 129.8, 129.1, 43.1, 21.4; anal. calcd for C16H18S2:
C, 70.02; H, 6.61; S, 23.37 %. Found: C, 70.16; H, 6.52; S,
23.32 %.
Bis(2-methyl-2-propenyl) disulfide (2e) colorless oil;
1
HNMR (250 MHz, CDCl3): δ 1.80 (s, 6H), 3.27 (s,
4H), 4.77–4.86 (m, 4H); 13CNMR (62.5 MHz, CDCl3):
δ  = 141.0, 115.1, 46.6, 20.7; anal. calcd for C8H14S2: C,
55.12; H, 8.09; S, 36.79 %. Found: C, 55.21; H, 7.96; S,
36.83 %.
Octyl disulfide (2  h) colorless oil; 1HNMR (250 MHz,
CDCl3): δ  = 0.83–0.89 (m, 6H), 1.27–1.36 (m, 20H),
1.53–1.68 (m, 4H), 2.64 (t, J  = 7.3 Hz, 4H); 13CNMR
(62.5 MHz, CDCl3): δ = 39.2, 31.7, 29.4, 29.2, 29.1, 28.6,
22.7, 14.1; Anal. Calcd for C16H34S2: C, 66.14; H, 11.79; S,
22.07 %. Found: C, 66.10; H, 11.74; S, 22.16 %.
Decyl disulfide (2  k) colorless oil; 1HNMR (250 MHz,
CDCl3): δ = 0.80–0.85 (m, 6H), 1.21–1.35 (m, 28H), 1.59–
1.73 (m, 4H), 2.64 (t, J = 7.3 Hz, 4H); 13CNMR (62.5 MHz,
CDCl3): δ  = 39.2, 31.8, 29.6, 29.5, 29.3, 29.2, 29.0, 28.5,
22.8, 14.2; anal. calcd for C20H42S2: C, 69.29; H, 12.21; S,
18.50 %. Found: C, 69.41; H, 12.13; S, 18.46 %.
Cyclohexyl disulfide (2n) colorless oil; 1HNMR
(250 MHz, CDCl3): δ 1.17–1.31 (m, 10H), 1.52–1.64 (m,
2H), 1.70–1.82 (m, 4H), 1.99–2.06 (m, 4H), 2.64–2.73 (m,
2H); 13CNMR (62.5 MHz, CDCl3): δ  = 50.1, 32.7, 26.1,
25.7; anal. calcd for C12H22S2: C, 62.55; H, 9.62; S, 27.83.
Found: C, 62.39; H, 9.75; S, 27.86 %.
n-Propyl disulfide (2f) colorless oil; 1HNMR
(250 MHz, CDCl3): δ  = 0.99(t, J  = 7.4 Hz, 6H), 1.71
(sext, J = 7.4 Hz, 4H), 2.66 (t. J = 7.4 Hz, 4H); 13CNMR
(62.5 MHz, CDCl3): δ  = 13.1, 22.5, 41.2; anal. calcd for
C6H14S2: C, 47.95; H, 9.39; S, 42.66. Found: C, 47.82; H,
9.50; S, 42.68 %.
iso-Propyl disulfide (2  k) colorless oil: 1HNMR
(250 MHz, CDCl3): δ  = 1.30 (d, J  = 6.9 Hz, 12H), 2.97
(sept, J  = 6.9 Hz, 2H); 13CNMR (62.5 MHz, CDCl3):
δ = 22.6, 41.4); anal. calcd for C6H14S2: C, 47.95; H, 9.39;
S, 42.66. Found: C, 48.04; H, 9.44; S, 42.52 %.
Conclusion
In conclusion, we have developed a one-pot and odorless
preparation of disulfides from alkyl halides using thiourea
as a cheap and available sulfur surrogate and CCl4 in the
presence of Et3N under mild conditions. Various primary
and secondary, allylic and benzylic halides can be effec-
tively used to produce the corresponding symmetrical
disulfides in good to excellent yields.
Acknowledgments  We gratefully acknowledge the support of this
study by the Persian Gulf University and Shiraz University Research
Council.
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