A traceless, one-pot preparation of unsymmetric disulfides from symmetric disulfides through a repeated process involving sulfenic acid and thiosulfinate intermediates

Tetrahedron Letters

Volumn 52, Issue 2, 2011, Pages 236-239

  Han, Minsoo ^a   Lee, Jong Tak ^a   Hahn, Hoh Gyu ^a  

^a Korea Institute of Science and Technology   (South Korea)

Author keywords

Sulfenic acid; Thiosulfinate; Unsymmetric disulfide

Indexed keywords

CHLORIDE; DISULFIDE; SULFENIC ACID DERIVATIVE; SULFURYL CHLORIDE; THIOL DERIVATIVE; TRIAZOLYL PHENYL DISULFIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; ONE POT SYNTHESIS;

EID: 78650008691     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.042     Document Type: Article

References (38)

1. S.H. Lee Arch. Pharm. Res. 32 2009 299
2. E. Block Angew. Chem., Int. Ed. Engl. 31 1992 1135
3. A. Vogt, K. Tamura, S. Watson, and J.S. Lazo J. Pharmacol. Exp. Ther. 294 2000 1070
4. D. Witt Synthesis 16 2008 2491
5. N.E. Heimer J. Org. Chem. 50 1985 4164
6. G. Derbesy, and D.N. Harpp Tetrahedron Lett. 35 1994 5381
7. M. Bao, and M. Shimizu Tetrahedron 59 2003 9655
8. K.S. Boustany, and A.B. Sullivan Tetrahedron Lett. 11 1970 3547
9. T. Mukaiyama, and K. Takahashi Tetrahedron Lett. 56 1968 5907 5908
10. G.R. Morais, and R.A. Falconer Tetrahedron Lett. 48 2007 7637
11. R. Hunter, M. Caira, and N. Stellenboom J. Org. Chem. 71 2006 8268
12. M. Masui, Y. Mizuki, K. Sakai, C. Ueda, and H. Ohmori J. Chem. Soc., Chem. Commun. 13 1984 843
13. S.J. Brois, J.F. Pilot, and H.W. Barnum J. Am. Chem. Soc. 92 1970 7629
14. S. Oae, Y.H. Kim, D. Fukushima, and K. Shinhama J. Chem. Soc., Perkin Trans. 1 1978 913
15. A. Rajca, and M. Wiessler Tetrahedron Lett. 31 1990 6075
16. M. Ohtani, and N. Narisada J. Org. Chem. 56 1991 5475
17. E. Brzezinska, and A.L. Ternay J. Org. Chem. 59 1994 8239
18. D.H.R. Barton, R.H. Hesse, A.C. O'Sullivan, and M.M. Pechet J. Org. Chem. 56 1991 6697
19. D.H.R. Barton, C. Chen, and M.G. Wall Tetrahedron 47 1991 6127
20. K. Tanaka, and K. Ajiki Tetrahedron Lett. 45 2004 5677
21. M. Arisawa, and M. Yamaguchi J. Am. Chem. Soc. 125 2003 6624
22. K. Görmer, H. Waldmann, and G. Triola J. Org. Chem. 75 2010 1811
23. K. Goto, N. Tokitoh, and R. Okazaki Angew. Chem., Int. Ed. Engl. 34 1995 1124
24. J.L. Kice, L. Weclas-Henderson, and A. Kewan J. Org. Chem. 54 1989 4198
25. P.E. Penn, E. Block, and L.K. Revelle J. Am. Chem. Soc. 100 1978 3622
26. D.R. Hogg Sulphenic Acids and Their Derivatives 1st ed. D. Barton, W.D. Ollis, D.N. Jones, Comprehensive Organic Chemistry Vol. 3 1979 Pergamon Press Oxford 261 310
27. J.L. Kice, and T.E. Rogers J. Am. Chem. Soc. 96 1974 8015
28. J.J. Kice, and J.P. Cleveland J. Am. Chem. Soc. 92 1970 4757
29. J.L. Kice, and C.A. Liu J. Org. Chem. 44 1979 1918
30. J.L. Kice, and G.B. Large J. Org. Chem. 33 1968 1940
31. G. Capozzi, A. Capperucci, A. DeInnocenti, R.D. Duce, and S. Menichetti Tetrahedron Lett. 30 1989 2995
32. T. Miron, I. Shin, G. Feigenblat, L. Weiner, D. Mirelman, M. Wilchek, and A. Rabinkov Anal. Biochem. 307 2002 76
33. D.R. Graber, R.A. Morge, and J.C. Sih J. Org. Chem. 52 1987 4620
34. G. Zhang, B. Li, C.H. Lee, and K.L. Parkin J. Agric. Food Chem. 58 2010 1564
35. F. Freeman, and C.N. Angeletakis J. Org. Chem. 50 1985 793 798
36. F. Freeman, and C.N. Angeletakis J. Org. Chem. 46 1981 3991
37. R.B. Cody, J.A. Laramee, and H.D. Durst Anal. Chem. 77 2005 2297
38. 2 calculations.