A one-pot, efficient, and odorless synthesis of symmetrical disulfides using organic halides and thiourea in the presence of manganese dioxide and wet polyethylene glycol (PEG-200)

Tetrahedron Letters

Volumn 51, Issue 3, 2010, Pages 508-509

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Abbasi, Mohammad ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; MACROGOL 200; MANGANESE DIOXIDE; ORGANOHALOGEN DERIVATIVE; SULFUR; THIOUREA;

ARTICLE; CHEMICAL STRUCTURE; ODOR; ONE POT SYNTHESIS; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 71649095877     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.060     Document Type: Article

References (39)

1. Bodanszky M. Principles of Peptide Synthesis (1984), Springer, Berlin Chapter 4
2. Johnson J.R., Bruce W.F., and Dutcher J.D. J. Am. Chem. Soc. 65 (1943) 2005-2009
3. Sonavane S.U., Chidambaram M., Almog J., and Sasson Y. Tetrahedron Lett. 48 (2007) 6048-6050
4. Sudharsanam R., Chandrasekaran S., and Das P.K. J. Mater. Chem. 12 (2002) 2904-2908
5. Haas U., Thalacker C., Adams J., Fuhrmann J., Riethmuller S., Beginn U., Ziener U., Moller M., Dobrawa R., and Wurthner F. J. Mater. Chem. 13 (2003) 767-772
6. Shirani H., and Janosik T. Synthesis (2007) 2690-2698
7. Atkinson J.G., Hamel P., and Yves Girard Y. Synthesis (1988) 480-481
8. Movassagh B., and Zakinezhad Y. Z. Naturforsch. 61b (2006) 47-49
9. Ranu B.C., and Mandal T. Synlett (2004) 1239-1242
10. Bartolozzi A., Foudoulakis H.M., and Cole B.M. Synthesis (2008) 2023-2032
11. Prabhu K.R., Sivanand P.S., and Chandrasekaran S. Angew. Chem., Int. Ed. 39 (2000) 4316-4319
12. Movassagh B., Sobhani S., Kheirdoush F., and Fadaei Z. Synth. Commun. 33 (2003) 3103-3108
13. Kodama S., Nishinaka E., Nomoto A., Sonoda M., and Ogawa A. Tetrahedron Lett. 48 (2007) 6312-6317
14. Kondo T., and Mitsudo T. Chem. Rev. 100 (2000) 3205-3220
15. Yamagiwa N., Suto Y., and Torisawa Y. Bioorg. Med. Chem. Lett. 17 (2007) 6197-6201
16. Taniguchi N. Synlett (2008) 849-852
17. Kirihara M., Asai Y., Ogawa S., Noguchi T., Hatano A., and Hirai Y. Synthesis (2007) 3286-3289
18. Golchoubian H., and Hosseinpoor F. Catal. Commun. 8 (2007) 697-700
19. Kirihara M., Okubo K., Uchiyama T., Kato Y., Ochiai Y., Matsushita S., Hatano A., and Kanamori K. Chem. Pharm. Bull. 52 (2004) 625-627
20. Silveira C.C., and Mendes S.R. Tetrahedron Lett. 48 (2007) 7469-7471
21. Lenardao E.J., Lara R.G., Silva M.S., Raquel G., Jacob R.G., and Perin G. Tetrahedron Lett. 48 (2007) 7668-7670
22. Ali M.H., and McDermott M. Tetrahedron Lett. 43 (2002) 6271-6273
23. Akdag A., Webb T., and Worley S.D. Tetrahedron Lett. 47 (2006) 3509-3510
24. Iranpoor N., and Zeynizadeh B. Synthesis (1999) 49-50
25. Firouzabadi H., Abbassi M., and Karimi B. Synth. Commun. 29 (1999) 2527-2531
26. Iranpoor N., Firouzabadi H., and Pourali A.R. Tetrahedron 58 (2002) 5179-5184
27. Witt D. Synthesis (2008) 2491-2509 and references cited therein
28. Hase T.A., and Perakyla H. Synth. Commun. 12 (1982) 947-950
29. Wang J.-X., Gao L., and Huang D. Synth. Commun. 32 (2002) 963-969
30. Gladysz J.A., Wong V.K., and Jick B.S. Tetrahedron 35 (1979) 2329-2335
31. Wang J.-X., Cui W., and Hu Y. Synth. Commun. 25 (1995) 3573-3581
32. Srivatava P.K., Chandra R., and Gupta M.B. Curr. Sci. 51 (1982) 692-695
33. Bandgar B.P., Uppalla L.S., and Sadavarte V.S. Tetrahedron Lett. 42 (2001) 6741-6743
34. Emerson D.W., Bennett B.L., and Steinberg S.M. Synth. Commun. 35 (2005) 631-638
35. Chen J., Spear S.K., Huddleston J.G., and Rogers R.D. Green Chem. 7 (2005) 64-82
36. Firouzabadi H., and Ghaderi E. Tetrahedron Lett. 19 (1978) 839-840
37. Firouzabadi H., and Mostafavipoor Z. Bull. Chem. Soc. Jpn. 56 (1983) 914-917
38. 4, filtered, and concentrated to yield the crude product, which was further purified by silica gel chromatography using low-boiling petroleum ether as an eluent to provide the desired product in 65-88% yields.
39. 2: C, 66.14; H, 11.79; S, 22.07. Found: C, 66.21; H, 11.71; S, 22.08.