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493
24. (a) Kamal, A.; Chouhan, G. Tetrahedron Lett. 2005, 46, 1489; (b) Mohanazadeh,
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Acknowledgments
25. Tamura, Y.; Kawasaki, T.; Adachi, M.; Tanio, M.; Kita, Y. Tetrahedron Lett. 1977,
4417.
We thank Shahid Chamran University Research Council, Ahvaz,
for the financial support of this investigation. We also thank Dr. I.
Kazemi-Nezhad for running the NMR spectra.
26. (a) Iranpoor, N.; Firouzabadi, H.; Shaterian, H. R. J. Chem. Res. 1999, 1, 676; (b)
Iranpoor, N.; Firouzabadi, H.; Shaterian, H. R. Synlett 2000, 65; (c) Iranpoor, N.;
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27. (a) Iranpoor, N.; Firouzabadi, H.; Akhlaghinia, B.; Azadi, R. Synthesis 2004, 92;
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References and notes
28. Iranpoor, N.; Firouzabadi, H.; Nowrouzi, N. Tetrahedron 2006, 62, 5498.
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30. (a) Mokhtari, B.; Azhdari, A.; Azadi, R. J. Sulfur Chem. 2009, 30, 585; (b)
Mokhtari, B.; Azadi, R.; Rahmani-Nezhad, S. Tetrahedron Lett. 2009, 50, 6588.
31. Procedure for the preparation of MTPI: To a solution of CMPI (0.255 g, 1 mmol)
in CH3CN (5 ml), NH4SCN (0.076 g, 1 mmol) was added at room temperature.
The mixture was stirred for 1 h to form a white solid (NH4Cl). The mixture was
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then filtered and the solvent was evaporated under vacuum in
a rotary
evaporator to afford the pure MTPI in high yield (95%) as a white solid. Further
purification can be achieved by chromatography on a short column of silica gel
using n-hexane/EtOAc (6:3) as eluent. IR (-SCN) in CCl4 2160.78 cmÀ1 1H NMR
;
(400 MHz, CDCl3) d 3.99 (3H, s), 6.64–6.67 (1H, t) 7.19–7.23 (1H, t), 7.68–7.72
(2H, t) ppm; 13C NMR (100 MHz, CDCl3) d 180.30, 145.66, 140.85, 136.05,
134.14, 113.46, 46.12 ppm.
32. General procedure for the one-pot preparation of alkyl thiocyanates in the
presence of CMPI/NH4SCN in CH3CN: To a solution of CMPI (0.510 g, 2 mmol) in
CH3CN (10 mL) was added NH4SCN (0.152 g, 2 mmol) at room temperature and
the mixture was stirred for 45 min to form a white solid. Then, alcohol (1 mmol)
was added and the mixture stirred for the appropriate amount of time (Table 1).
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H2O was added and the organic layer extracted with Et2O (3 Â 5 mL). The
combined organic extracts were dried (Na2SO4). Evaporation of the solvent and
chromatography on a short silica gel column using n-hexane/EtOAc (5:1) as
eluent gave the corresponding alkyl thiocyanate.
33. General procedure for solvent-free preparation of alkyl thiocyanates using of
CMPI/NH4SCN/alcohol: The preparation of the alkyl thiocyanate was carried
out by grinding CMPI (0.510 g, 2 mmol) and NH4SCN (0.152 g, 2 mmol) in a hot
mortar for 1 min (the mortar was preheated in an oven for 2 h at 100 °C). Next
the alcohol (1 mmol) was added to the mixture and grinding was continued for
an additional 3–4 min. After completion of the reaction, H2O was added and
the organic layer extracted with Et2O (3 Â 5 mL). The combined organic
extracts were dried (Na2SO4). Evaporation of the solvent and chromatography
on a short silica gel column using n-hexane/EtOAc (5:1) as eluent gave the
corresponding alkyl thiocyanate.
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