Phosphine-assisted rearrangement of 4,5-dihydroxy-1,2-dithianes to 4-hydroxy-3-mercaptotetrahydrothiophenes

Heterocycles

Volumn 60, Issue 1, 2003, Pages 47-56

  Lee, Sang Hyup ^a   Kohn, Harold ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIANE 4,5 DIOL; 4 HYDROXY 3 MERCAPTOTETRAHYDROTHIOPHENE; DISULFIDE; HETEROCYCLIC COMPOUND; HYDROXYL GROUP; PHOSPHINE DERIVATIVE; TETRAHYDROTHIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIASTEREOISOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0037246865     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-02-9603     Document Type: Article

References (38)

1. H. D. Hartough 'The Chemistry of Heterocyclic Compounds; Thiophene and Its Derivatives' ed. by A. Weissberger, Intersciences, New York, 1952, pp. 76-78; T. Eicher and S. Hauptmann, 'The Chemistry of Heterocycles: Structure, Reactions, Syntheses and Applications' George Thieme Verlag Stuttgart, New York, New York, 1995, pp. 84-85.
2. H. D. Hartough 'The Chemistry of Heterocyclic Compounds; Thiophene and Its Derivatives' ed. by A. Weissberger, Intersciences, New York, 1952, pp. 76-78; T. Eicher and S. Hauptmann, 'The Chemistry of Heterocycles: Structure, Reactions, Syntheses and Applications' George Thieme Verlag Stuttgart, New York, New York, 1995, pp. 84-85.
3. T. Naka, N. Nishizono, N. Minakawa, and A. Matsuda, Tetrahedron Lett., 1999, 40, 6297; J. E. McCormick and R. S. McElhinney, J. Chem. Soc., Perkin Trans. I, 1976, 2533.
4. T. Naka, N. Nishizono, N. Minakawa, and A. Matsuda, Tetrahedron Lett., 1999, 40, 6297; J. E. McCormick and R. S. McElhinney, J. Chem. Soc., Perkin Trans. I, 1976, 2533.
5. J. E. McCormick and R. S. McElhinney, J. Chem. Soc., Perkin trans. I, 1972, 2795; V. Glaçon, M. Benazza, D. Beaupère, and G. Demailly, Tetrahedron Lett., 2000, 41, 5053.
6. J. E. McCormick and R. S. McElhinney, J. Chem. Soc., Perkin trans. I, 1972, 2795; V. Glaçon, M. Benazza, D. Beaupère, and G. Demailly, Tetrahedron Lett., 2000, 41, 5053.
7. R. A. Sanchez, Synthesis, 1982, 148.
8. W. W. Cleland, Biochemistry, 1964, 3, 480; M. Carmack and C. J. Kelley, J. Org. Chem., 1968, 33, 2171.
9. W. W. Cleland, Biochemistry, 1964, 3, 480; M. Carmack and C. J. Kelley, J. Org. Chem., 1968, 33, 2171.
10. S. Capasso, I. Mazzarella, and A. Zagari, J. Cryst. & Spectros. Res., 1984, 14, 303.
11. C. A. Evans, L. Bernier, J. Dugas, and T. S. Mansour, Tetrahedron Lett., 1977, 38, 7657.
12. J. A. Burns, J. C. Butler, J. Moran, and G. M. Whitesides, J. Org. Chem., 1991, 56, 2648; M. R. Levison, A. S. Josephson, and D. M. Kirschenbaum, Experientia, 1968, 25, 126.
13. J. A. Burns, J. C. Butler, J. Moran, and G. M. Whitesides, J. Org. Chem., 1991, 56, 2648; M. R. Levison, A. S. Josephson, and D. M. Kirschenbaum, Experientia, 1968, 25, 126.
14. L. E. Overman, D. Matzinger, E. M. O'Connor, and J. D. Overman, J. Am. Chem. Soc., 1974, 96, 6081; L. E. Overman and S. T. Petty, J. Org. Chem., 1975, 40, 2779.
15. L. E. Overman, D. Matzinger, E. M. O'Connor, and J. D. Overman, J. Am. Chem. Soc., 1974, 96, 6081; L. E. Overman and S. T. Petty, J. Org. Chem., 1975, 40, 2779.
16. L. E. Overman and E. M. O'Connor, J. Am. Chem. Soc., 1976, 98, 771.
17. A. J. Parker and N. Kharasch, J. Am. Chem. Soc., 1960, 82, 3071; J. L. Kice, 'Sulfur in Organic and Inorganic Chemistry' Vol. 1, ed. by A. Senning, Marcel Dekker, New York, NY, 1971, Chapter 6.
18. A. J. Parker and N. Kharasch, J. Am. Chem. Soc., 1960, 82, 3071; J. L. Kice, 'Sulfur in Organic and Inorganic Chemistry' Vol. 1, ed. by A. Senning, Marcel Dekker, New York, NY, 1971, Chapter 6.
19. J. Skarżewski and A. Gupta, Tetrahedron Asymmetry, 1997, 8, 1861; H. Dulphy, J.-L. Gras, and T. Lejon, Tetrahedron, 1996, 52, 8517; A. H. Haines, K. C. Symes, and A. G. Wells, Carbohydr. Res., 1975, 41, 85.
20. J. Skarżewski and A. Gupta, Tetrahedron Asymmetry, 1997, 8, 1861; H. Dulphy, J.-L. Gras, and T. Lejon, Tetrahedron, 1996, 52, 8517; A. H. Haines, K. C. Symes, and A. G. Wells, Carbohydr. Res., 1975, 41, 85.
21. J. Skarżewski and A. Gupta, Tetrahedron Asymmetry, 1997, 8, 1861; H. Dulphy, J.-L. Gras, and T. Lejon, Tetrahedron, 1996, 52, 8517; A. H. Haines, K. C. Symes, and A. G. Wells, Carbohydr. Res., 1975, 41, 85.
22. R. G. Ritchie, N. Cyr, B. Korsch, H. J. Koch, and A. S. Perlin, Can. J. Chem., 1975, 53, 1424.
23. A. S. Perlin and H. J. Koch, Can. J. Chem., 1970, 48, 2639.
24. D. M. Grant and B. V. Cheney, J. Am. Chem. Soc., 1967, 89, 5315; D. K. Dalling and D. M. Grant J. Am. Chem. Soc., 1967, 89, 6612; D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 1972, 94, 5318.
25. D. M. Grant and B. V. Cheney, J. Am. Chem. Soc., 1967, 89, 5315; D. K. Dalling and D. M. Grant J. Am. Chem. Soc., 1967, 89, 6612; D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 1972, 94, 5318.
26. D. M. Grant and B. V. Cheney, J. Am. Chem. Soc., 1967, 89, 5315; D. K. Dalling and D. M. Grant J. Am. Chem. Soc., 1967, 89, 6612; D. K. Dalling and D. M. Grant, J. Am. Chem. Soc., 1972, 94, 5318.
27. S. Cortes and H. Kohn, J. Org. Chem., 1983, 48, 2246; J. P. Monti, R. Faure, and E. Vincent, J. Org. Magn. Reson., 1976, 8, 611.
28. S. Cortes and H. Kohn, J. Org. Chem., 1983, 48, 2246; J. P. Monti, R. Faure, and E. Vincent, J. Org. Magn. Reson., 1976, 8, 611.
29. A. Schönberg and M. Z. Barakat, J. Chem. Soc., 1949, Part II, 892; J. T. Ayers and S. R. Anderson, Syn. Commun., 1999, 29, 351.
30. A. Schönberg and M. Z. Barakat, J. Chem. Soc., 1949, Part II, 892; J. T. Ayers and S. R. Anderson, Syn. Commun., 1999, 29, 351.
31. B. J. Sweetman and J. A. Maclaren, Aust. J. Chem., 1966, 19, 2347; J. A. Maclaren and B. J. Sweetman, Aust. J. Chem., 1966, 19, 2355.
32. B. J. Sweetman and J. A. Maclaren, Aust. J. Chem., 1966, 19, 2347; J. A. Maclaren and B. J. Sweetman, Aust. J. Chem., 1966, 19, 2355.
33. B. Kim, M. Kodomari, and S. L. Regen, J. Org. Chem., 1984, 49, 3233; R. A. Amos and S. M. Fawcett, J. Org. Chem., 1984, 49, 2637.
34. B. Kim, M. Kodomari, and S. L. Regen, J. Org. Chem., 1984, 49, 3233; R. A. Amos and S. M. Fawcett, J. Org. Chem., 1984, 49, 2637.
35. J. Brånalt, I. Kvarnström, B. Classon, and B. Samuelsson, J. Org. Chem., 1996, 61, 3611.
36. M. Grayson and C. E. Farley, Chem. Commun., 1967, 831.
37. Attempts to extend this transformation for the preparation of other heterocycles were unsuccessful. We observed disulfide conversion to the corresponding thiol when 7 was added to 3- hydroxypropyl disulfide, 4-hydroxybutyl disulfide, 2′,2′-dithioethanoic acid, 3,3′-dithiopropanoic acid, and N,N′-di-Cbz-cystamine.
38. For a related transformation, see: F. P. Doyle, D. O. Holland, K. R. L. Mansford, J. H. C. Nayler, and A. Queen, Antituberculous Sulfur Compounds. II. Some Cyclic Sulfides Derived from Dimercaptoalkanols, J. Chem. Soc., 1960, 2660.