The acid-catalysed rearrangements of 4,5-bis(2-thienylhydroxymethyl)-1,3-dithiole-2-thione

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 7, 1999, Pages 1405-1410

  Serebryakov, Igor M ^a   Skabara, Peter J ^a   Perepichka, Igor F ^b  

^a SHEFFIELD HALLAM UNIVERSITY   (United Kingdom)

^b L M LITVINENKO INSTITUTE OF PHYSICAL ORGANIC AND COAL CHEMISTRY   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005938671     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901178a     Document Type: Article

References (32)

1. (a) I. C. Bateman and E. D. Hughes, J. Chem. Soc., 1940, 945;
2. (b) M. Fujio, K. Nagatta, Y. Tsuji, T. Otsu and Y. Tsuno, Tetrahedron Lett., 1992, 3, 321.
3. I. Lee. Y. S. Lee and H. W. Lee, J. Chem. Soc., Perkin Trans. 2, 1993, 1441.
4. (a) J. W. Hill and A. Fry, J. Am. Chem. Soc., 1962, 84, 2763;
5. (b) A. Fry, in Isotope Effects in Chemical Reactions (ACS Monograph 167), ed. C. J. Collins and N. S. Bowman, Van Nostrand, New York, 1971, pp. 373-383.
6. (a) T. W. Bentley, I. S. Koo and S. J. Norman, J. Org. Chem., 1991, 56, 1604;
7. (b) D. N. Kevill, N. H. Ismail and M. J. D'Souza, J. Org. Chem., 1994, 59, 6303.
8. P. J. Skabara, I. M. Serebryakov, D. M. Roberts, I. F. Perepichka, S. J. Coles and M. B. Hursthouse, J. Org. Chem., in press.
9. W. G. Young, S. Winstein and H. L. Goering, J. Am. Chem. Soc., 1951, 73, 1958.
10. A. J. Thibblin, J. Chem. Soc., Perkin Trans. 2, 1987, 1629.
11. See, for example, N. Pirincciolgu and A. Thibblin, J. Am. Chem. Soc., 1998, 120, 6512 and references cited therein.
12. G. V. D. Tiers, J. Chem. Phys., 1958, 29, 963.
13. S. C. Datta, J. N. Day and C. K. Ingold, J. Chem. Soc., 1939, 838.
14. J. Mindl and M. Vecera, Collect. Czech. Chem. Commun., 1970, 35, 3621.
15. A. A. Deniz, B. Li and K. S. Peters, J. Phys. Chem., 1995, 99, 12209.
16. S. Winstein, P. E. Klinedist and G. C. Robinson, J. Am. Chem. Soc., 1958, 80, 885.
17. K.-T. Liu, Y-F. Duann and S.-J. Hou, J. Chem. Soc., Perkin Trans. 2, 1998, 2181.
18. J. Bartl, S. Steenken, H. Mayr and R. A. McClelland, J. Am. Chem. Soc., 1990, 112, 6918.
19. A. Thibblin, J. Am. Chem. Soc., 1984, 106, 183.
20. (a) T. Kinoshita, T. Ueno, K. Ikai, M. Fujiwara and K. Okamoto, Bull. Chem. Soc. Jpn., 1988, 61, 3273;
21. (b) I. M. Serebryakov, I. V. Shpan'ko and N. M. Olejnik, Org. React. (Tartu), 1993, 28, 6.
22. T. L. Amyes, J. P. Richard and M. Novar, J. Am. Chem Soc., 1992, 114, 8032.
23. For an overview, see: C. K. Ingold, Structure and reactivity in organic chemistry, Bell & Sons, London, 1969, pp. 794-837.
24. L. Melander and W. H. Sonders, Reaction Rates of Isotopic Molecules, Wiley, New York, 1980.
25. (a) Y. Pocker, J. Chem. Soc., 1959, 3939;
26. (b) H. L. Goering and H. Hopf, J. Am. Chem Soc., 1971, 93, 1224;
27. (c) F. L. Schadt, T. W. Bentley and P. v. R. Schleyer, J. Am. Chem. Soc., 1976, 98, 7667;
28. (d) D. J. McLennan and P. L. Martin, J. Chem. Soc., Perkin Trans. 2, 1982, 1091;
29. (e) J. P. Richard and W. P. Jencks, J. Am. Chem. Soc., 1984, 106, 1383;
30. (f) A. R. Stein, Can. J. Chem., 1987, 65, 363;
31. (g) I. Lee, H. Y. Kim, H. K. Rang and H. W. Lee, J. Org. Chem., 1988, 53, 2678.
32. A. W. M. Lee, W. H. Chan and H. C Wong, Synth. Commun., 1988, 18, 1531.