PHOSPHORUS, SULFUR, AND SILICON
69
Scheme . A proposed mechanism for conversion of epoxides to thiiranes by use of alumina immobilized thiourea.
eluent. After completion of the reaction, the mixture was washed 15. Salehi, P.; Khodaei, M. M.; Zolfigol, M. A.; Keyvan, A. Synth. Commun.
2003, 33, 3041-3048.
with EtOAc (3 × 5 mL). The combined washing solvents were
16. Firouzabadi, H.; Iranpoor, N.; Khoshnood, A. J. Mol. Catal. A: Chem.
evaporated under reduced pressure to give the crude thiirane for
2007, 274, 109-115.
17. Reddy, C. S.; Nagavani, S. Heteroatom Chem. 2008, 19, 97-99.
18. Bandgar, B. P.; Patil, A. V.; Kamble, V. T.; Totre, J. V. J. Mol. Catal. A:
Chem. 2007, 273, 114-117.
further purification by a short-column chromatography over sil-
19. Yadav, J. S.; Subba Reddy, B. V.; Sengupta, S.; Gupta, M. K.; Baishya,
G.; Harshavardhana, S. J.; Dash, U. Monatsh. Chem. 2008, 139, 1363-
1367.
20. Kazemi, F.; Kiasat, A. R. Phosphorus Sulfur Silicon Relat. Elem. 2003,
178, 1333-1337.
21. Mohammadpoor-Baltork, I.; Aliyan, H. J. Chem. Res. 2000, 122-123.
22. Kazemi, F.; Kiasat, A. R.; Ebrahimi, S. Synth. Commun. 2003, 33, 595-
600.
23. Bandgar, B. P.; Joshi, N. S.; Kamble, V. T. Tetrahedron Lett. 2006, 47,
4775-4777.
Recovery of alumina
After extraction of the crude thiirane, distilled water (15 mL)
was added to the reaction vessel followed by stirring for 5 min
at room temperature. The alumina was filtered and then dried
in an oven for 2 h at 100 °C. The recycled alumina can be reused
for immobilization of thiourea.
24. Mirkhani, V.; Tangestaninejad, S.; Alipanah, L. Synth. Commun 2002,
32, 621-626.
Funding
25. Yadav, J. S.; Subba Reddy, B. V.; Reddy, C. S.; Rajasekhar, K. J. Org.
Chem. 2003, 68, 2525-2527.
26. Surendra, K.; Krishnaveni, N. S.; Rama Rao, K. Tetrahedron Lett. 2004,
45, 6523-6526.
Financial support of this work by the Research Councils of Urmia and
Payame Noor Universities is gratefully acknowledged.
27. Tamami, B.; Borujeny, K. P.; Synth. Commun. 2004, 34, 65-70.
28. Tamami, B.; Kolahdoozan, M. Tetrahedron Lett. 2004, 45, 1535-
1537.
29. Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Shaibani, R. Tetra-
hedron 2004, 60, 6105-6111.
30. Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-
Baltork, I.; Taghavi, S. A. Catal. Commun. 2007, 8, 2087-2095.
31. Wu, L.; Wang, Y.; Yan, F.; Yang, C. Bull. Korean Chem. Soc. 2010, 31,
1419-1420.
References
1. Iranpoor, N.; Firouzabadi, H.; Chitsazi, M.; Jafari, A. A. Tetrahedron
2002, 58, 7037-7042.
2. Dittmer, D. C. In: A. R. Katritzky, C. W. Rees (Eds.), Comprehensive
Heterocyclic Chemistry; Pergamon: New York, 1984, 7, p. 132.
3. Vedejs, E.; Krafft, G. A. Tetrahedron 1982, 38, 2857-2881.
4. Kiasat, A. R.; Kazemi, F.; Fallah-Mehrjardi, M. Phosphorus Sulfur Sili-
con Relat. Elem. 2004, 179, 1841-1844.
5. Takido, T.; Kobayashi, Y.; Itabashi, K. Synthesis 1986, 779-780.
6. (a) Bouda, H.; Borredon, M. E.; Delmas, M.; Gaset, A. Synth. Commun.
1987, 17, 943-951;(b) Jankowski, K.; Harvey, R. Synthesis 1972, 627-
628;(c) Sander, M. Chem. Rev. 1966, 66, 297-339.
7. Tamami, B.; Kiasat, A. R. Synth. Commun. 1996, 26, 3953-3958.
8. Brimeyer, M. O.; Mehrota, A.; Quici, S.; Nigam, A.; Regen, S. L. J. Org.
Chem. 1980, 45, 4254-4255.
32. Zeynizadeh, B.; Yeghaneh, S. Phosphorus Sulfur Silicon Relat. Elem.
2008, 183, 2280-2286.
33. Zeynizadeh, B.; Yeghaneh, S. Phosphorus Sulfur Silicon Relat. Elem.
2009, 184, 362-368.
34. Kaboudin, B.; Norouzi, H. Synthesis 2004, 2035-2039.
35. Akhlaghinia, B.; Rahimizadeh, M.; Eshghi, H.; Zhaleh, S.; Rezazadeh,
S. J. Sulfur Chem. 2012, 33, 351-361.
9. Iranpoor, N.; Firouzabadi, H.; Jafari, A. A. Phosphorus, Sulfur, Silicon
Relat. Elem. 2005, 180, 1809-1814.
10. Eisavi, R.; Zeynizadeh, B.; Baradarani, M. M. Phosphorus Sulfur Silicon
Relat. Elem. 2011, 186, 1902-1909.
11. Zeynizadeh, B.; Baradarani, M. M.; Eisavi, R. Phosphorus Sulfur Silicon
Relat. Elem. 2011, 186, 2208-2215.
12. Yadav, J. S.; Subba Reddy, B. V.; Baishya, G. Synlett 2003, 396-398.
13. Yadollahi, B.; Tangestaninejad, S.; Habibi, M. H.Synth. Commun. 2004,
34, 2823-2827.
36. Mirza-Aghayan, M.; Molaee Tavana, M. J. Sulfur Chem. 2015, 36, 30-
35.
37. (a) Danks, T. N.; Desai, B. Green Chem. 2002, 4, 179-180; (b)
Kaboudin, B.; Nazari, R. Tetrahedron Lett. 2001, 42, 8211-8213; (c)
Kaboudin, B. Chem. Lett. 2001, 880-881.
38. (a) Kiasat, A. R.; Kazemi, F.; Fallah-Mehrjardi, M. J. Chin. Chem. Soc.
2007, 54, 1337-1339; (b) Kiasat, A. R.; Kazemi, F.; Fallah-Mehrjardi,
M. Asian J. Chem. 2005, 17, 2830-2832; (c) Schnurch, M.; Holzweber,
M.; Mihovilovic, M. D.; Stanetty, P. A Green Chem. 2007, 9, 139-145.
39. Lazlo, P. Preparative Chemistry Using Supported Reagents, Academic
Press: San Diego, CA, 1987, p. 387.
14. Mohammadpoor-Baltork, I.; Khosropour, A. R. Molecules 2001, 6,
996-1000.