Novel and efficient methods for the synthesis of symmetrical trisulfides

Synthesis

Volumn , Issue 9, 2009, Pages 1459-1462

  Kertmen, Ahmet ^b   Lach, Slawomir ^a   Rachon, Janusz ^a   Witt, Dariusz ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^b ESKISEHIR OSMANGAZI UNIVERSITY   (Turkey)

Author keywords

L cysteine; Sulfenyl bromides; Symmetrical trisulfides; Thiols

Indexed keywords

AROMATIC THIOL; EFFICIENT METHOD; GOOD YIELD; L-CYSTEINE; SULFENYL BROMIDES; SYMMETRICAL TRISULFIDES; THIOLS;

BROMINE COMPOUNDS; OPTICAL FILTERS;

SYNTHESIS (CHEMICAL);

(5,5 DIMETHYL 2 THIOXO 1,3,2 DIOXAPHOSPHORIN 2 YL)DISULFANYL DERIVATIVE; 11 [(5,5 DIMETHYL 2 THIOXO 1,3,2 DIOXAPHOSPHORINAN 2 YL)DISULFANYL]UNDECAN 1 OL; 11 [(5,5 DIMETHYL 2 THIOXO 1,3,2 DIOXAPHOSPHORINAN 2 YL)DISULFANYL]UNDECANE 1 OL; 5,5 DIMETHYL 2 SULFANYL 2 THIOXO 1,3,2 DIOXAPHOSPHORINANE; BIS(10 CARBOXYDECYL)TRISULFIDE; BIS(11 HYDROXYUNDECYL)TRISULFIDE; BIS(2 HYDROXYETHYL)TRISULFIDE; BIS(4 TOLYL)TRISULFIDE; BIS(5,5 DIMETHYL 2 THIOXO 1,3,2 DIOXAPHOSPHORINAN 2 YL)DISULFIDE; BIS[2 (TERT BUTOXYCARBONYLAMINO) 2 (ETHOXYCARBONYL)ETHYL]TRISULFIDE; DIDODECYL TRISULFIDE; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 67650082413     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088161     Document Type: Article

References (31)

1. (a) Higuchi, O.; Tateshita, K.; Nishimura, H. J. Agric. Food Chem. 2003, 51, 7208.
2. (b) Schregen, L.; Diriack, P.; Van Wassehove, F.; Schamp, N. J. Agric. Food Chem. 1976, 24, 336.
3. Nicolaou, K. C.; Hummel, C. W.; Nakada, M.; Shibayama, K.; Pitsinos, E. N.; Saimoto, H.; Mizuno, Y.; Baldenius, K.-U.; Smith, A. L. J. Am. Chem. Soc. 1993, 115, 7625.
4. Kumar, R. A.; Ikemoto, N.; Patel, D. J. J. Mol. Biol. 1997, 265, 173.
5. Schöberl, A.; Wagner, A. In Houben-Weyl, 4th ed., Vol. 9; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1955, 87-90.
6. (a) Zysman-Colman, E.; Harpp, D. N. J. Org. Chem. 2003, 68, 2487.
7. (b) Clayton, J. O.; Etzler, D. H. J. Am. Chem. Soc. 1947, 69, 974.
8. Fuson, R. C.; Price, C. h. C.; Burness, D. M.; Foster, R. E.; Hatchard, W. R.; Lipscomb, R. D. J. Org. Chem. 1946, 11, 487.
9. Sato, R.; Saito, S.; Chiba, H.; Goto, T.; Saito, M. Chem. Lett. 1986, 349.
10. Schimmelschmidt, K.; Hoffmann, H.; Mundlos, E. Chem. Ber. 1963, 96, 38.
11. Buckman, J. D.; Field, L. J. Org. Chem. 1967, 32, 2.
12. Mott, A. W.; Barany, G. Synthesis 1984, 657.
13. Hayashi, S.; Furukawa, M.; Yamamoto, J.; Hamamura, K. Chem. Pharm. Bull. 1967, 15, 1310.
14. Capozzi, G.; Capperucci, A.; Degl'Innocenti, A.; Del Duce, R.; Menichetti, S. Tetrahedron Lett. 1989, 30, 2991.
15. (a) Arisawa, M.; Tanaka, K.; Yamaguchi, M. Tetrahedron Lett. 2005, 46, 4797.
16. (b) Hou, Y.; Abu-Yousef, I. A.; Doung, Y.; Harpp, D. N. Tetrahedron Lett. 2001, 42, 8607.
17. Harpp, D. N.; Granata, A. Tetrahedron Lett. 1976, 17, 3001.
18. Wu, Z.; Back, T. G.; Ahmad, R.; Yamdagni, R.; Amstrong, D. A. J. Phys. Chem. 1982, 86, 4417.
19. An, H.; Zhu, J.; Wang, X.; Xu, X. Bioorg. Med. Chem. Lett. 2006, 16, 4826.
20. Nakabayashi, T.; Tsurugi, J. J. Org. Chem. 1961, 26, 2482.
21. Böhme, H.; Van Ham, G. Justus Liebigs Ann. Chem. 1958, 617, 62.
22. Harpp, D. N.; Derbesy, G. Tetrahedron Lett. 1994, 35, 5381.
23. Kresze, G.; Patzscheke, J. Chem. Ber. 1960, 93, 380.
24. Antoniow, S.; Witt, D. Synthesis 2007, 363.
25. Kowalczyk, J.; Barski, P.; Witt, D.; Grzybowski, B. A. Langmuir 2007, 23, 2318.
26. Szymelfejnik, M.; Demkowicz, S.; Rachon, J.; Witt, D. Synthesis 2007, 3528.
27. Demkowicz, S.; Rachon, J.; Witt, D. Synthesis 2008, 2033.
28. Pappo, D.; Kashman, Y. Org. Lett. 2006, 8, 1177.
29. Edmundson, R. S. Tetrahedron 1965, 21, 2379.
30. Carmona, E.; Contreras, L.; Sanches, L. J.; Gutierrez-Puebla, E.; Monge, A. J. Chem. Soc., Dalton Trans. 1989, 2003.
31. Kohama, Y.; Iida, K.; Semba, T.; Mimura, T.; Inada, A. Chem. Pharm. Bull. 1992, 40, 2210.