F
M. Soleiman-Beigi, Z. Arzehgar
Letter
Synlett
Dalton Trans. 2011, 40, 6344. (d) Deria, P.; Mondloch, J. E.;
Karagiaridi, O.; Bury, W.; Hupp, J. T.; Farha, O. K. Chem. Soc. Rev.
2014, 43, 5896.
Funding Information
Financial support from the Ilam University Research Council is grate-
fully acknowledged.
)(
(9) Furukawa, H.; Cordova, K. E.; O’Keeffe, M.; Yaghi, O. M. Science
2013, 341, 974.
(10) Dhakshinamoorthy, A.; Asiric, A. M.; Garcia, H. Chem. Soc. Rev.
2015, 44, 1922.
Supporting Information
(11) (a) Soleiman-Beigi, M.; Arzehgar, Z. Heteroat. Chem. 2015, 26,
355. (b) Soleiman-Beigi, M.; Yavari, I.; Sadeghizadeh, F. RSC Adv.
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Basereh, A. J. Sulfur Chem. 2017, 38, 572. (d) Soleiman-Beigi, M.;
Yavari, I.; Sadeghizadeh, F. Phosphorus, Sulfur Silicon Relat. Elem.
2018, 193, 41. (e) Soleiman-Beigi, M.; Mohammadi, F. J. Sulfur
Chem. 2016, 38, 134.
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Supporting information for this article is available online at
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References and Notes
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(14) General Procedure for the Synthesis of S-Alkyl Sulfurothio-
ates
The requisite alkyl halide (10.0 mmol) and sodium thiosulfate
pentahydrate (2.98 g, 12.0 mmol) dissolved in methanol–water
(3:1, 20 mL). The reaction mixture was stirred and heated to 65 °C.
Upon completion of the reaction, the mixture was cooled to
room temperature, and then concentrated at 40–45 °C. The
resultant solid was treated with methanol (50 mL), heated to 50 °C
(most solid dissolved), and filtered. This removed the excess
sodium thiosulfate and sodium chloride. The filtrate was con-
centrated to a white solid. The mixture was washed with n-
hexane, filtered, and dried under vacuum at 50 °C.
(15) General Procedure for the Synthesis of S-Aryl Sulfurothio-
ates
To a stirred mixture of iodobenzene (1.02 g, 5.0 mmol), sodium
thiosulfate pentahydrate (1.88 g, 7.5 mmol) and CuI (0.09 g, 0.5
mmol, 10 mol%) in DMSO (5 mL) was added 1,10-phenanthro-
line (0.18 g, 1.0 mmol, 20 mol%), and the mixture was stirred for
5 min at room temperature and then heated to 80 °C for 4 h
under a nitrogen atmosphere until completion of reaction. The
reaction mixture was cooled to room temperature, brine (15
mL) was added, and the mixture was stirred vigorously at room
temperature for 1 h. The mixture was filtered, and the solid was
washed successively with brine and n-hexanes. The solid was
dried under vacuum at 50 °C for 3 h.
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(16) General Procedure for the Synthesis of Unsymmetrical
Disulfides
The requisite alkyl (aryl) halide (1.0 mmol), potassium O-ethyl-
carbonodithioate (0.24 g, 1.5 mmol) and MOF-199 (4.0 mg)
were added to DMSO (2.0 mL) and the mixture heated to 80 °C
for 12 h. After complete conversion of the alkyl (aryl) halide into
O-ethyl-S-phenyl carbonodithioate, RS2O3Na (1.0 mmol) and
K2CO3 (0.14 g, 1.0 mmol) were added and the mixture heated to
80 °C for a further 12 h. The progress of reaction was monitored
by TLC. Upon completion of the reaction, the mixture was
cooled to room temperature and then filtered. The filtrate was
evaporated under vacuum, CH2Cl2 (20 mL) was added, and the
mixture was washed with H2O (2 × 15 mL). The combined
organic layers were dried over Na2SO4, filtered, and evaporated
to afford the crude unsymmettrical alkyl (aryl) disulfide, which
was purified by thick-layer chromatography (silica gel, eluting
wth n-hexane–ethyl acetate, 20:1; in the case of 5d,f,i,j,n,p,
4:1).
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O-Ethyl-S-phenyl Carbonodithioate (3)
Oil.1H NMR (300 MHz, CDCl3): δ = 7.76 (d, 2 HAr), 7.37–7.12 (m,
3 HAr), 3.26 (q, 2 HOEt), 1.14 (t, 3 HOEt) ppm.13C NMR (100
© Georg Thieme Verlag Stuttgart · New York — Synlett 2018, 29, A–G