Synthesis, isolation, and dimerization and trimerization of monosubstituted thiophene 1,1-dioxides

Heterocycles

Volumn 52, Issue 1, 2000, Pages 365-382

  Nakayama, Juzo ^a   Nagasawa, Hidehiro ^a   Sugihara, Yoshiaki ^a   Ishii, Akihiko ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OXIDE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033972245     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-S32     Document Type: Article

References (49)

1. J. Nakayama and Y. Sugihara, Top. Curr. Chem., in press (to appear in 1999, Vol. 205).
2. For other reviews, see S. Rajappa, in "Comprehenisve Heterocyclic Chemistry," Vol. 4, ed. by C. W. Bird and G. W. Cheeseman, Pergamon Press, Oxford, 1984, Chapter 3.14; S. Rajappa, in "Comprehenisve Heterocyclic Chemistry II," Vol. 2, ed. by C. W. Bird, Pergamon Press, Oxford, 1996, Chapter 2.10; M. S. Raasch, in "Thiophene and Its Derivatives," ed. by S. Gronowitz, John Wiley, New York, 1985, p. 571; N. S. Simpkins, "Sulfones in Organic Synthesis," Pergamon Press, Oxford, 1993, p. 319.
3. For other reviews, see S. Rajappa, in "Comprehenisve Heterocyclic Chemistry," Vol. 4, ed. by C. W. Bird and G. W. Cheeseman, Pergamon Press, Oxford, 1984, Chapter 3.14; S. Rajappa, in "Comprehenisve Heterocyclic Chemistry II," Vol. 2, ed. by C. W. Bird, Pergamon Press, Oxford, 1996, Chapter 2.10; M. S. Raasch, in "Thiophene and Its Derivatives," ed. by S. Gronowitz, John Wiley, New York, 1985, p. 571; N. S. Simpkins, "Sulfones in Organic Synthesis," Pergamon Press, Oxford, 1993, p. 319.
4. For other reviews, see S. Rajappa, in "Comprehenisve Heterocyclic Chemistry," Vol. 4, ed. by C. W. Bird and G. W. Cheeseman, Pergamon Press, Oxford, 1984, Chapter 3.14; S. Rajappa, in "Comprehenisve Heterocyclic Chemistry II," Vol. 2, ed. by C. W. Bird, Pergamon Press, Oxford, 1996, Chapter 2.10; M. S. Raasch, in "Thiophene and Its Derivatives," ed. by S. Gronowitz, John Wiley, New York, 1985, p. 571; N. S. Simpkins, "Sulfones in Organic Synthesis," Pergamon Press, Oxford, 1993, p. 319.
5. For other reviews, see S. Rajappa, in "Comprehenisve Heterocyclic Chemistry," Vol. 4, ed. by C. W. Bird and G. W. Cheeseman, Pergamon Press, Oxford, 1984, Chapter 3.14; S. Rajappa, in "Comprehenisve Heterocyclic Chemistry II," Vol. 2, ed. by C. W. Bird, Pergamon Press, Oxford, 1996, Chapter 2.10; M. S. Raasch, in "Thiophene and Its Derivatives," ed. by S. Gronowitz, John Wiley, New York, 1985, p. 571; N. S. Simpkins, "Sulfones in Organic Synthesis," Pergamon Press, Oxford, 1993, p. 319.
6. For generation and reactions (chemical trapping) of 1, see
7. a) H. J. Backer and J. L. Melles, Proc. Koninkl. Nederland Akad. Wetenschap., 1951, 54B, 340;
8. b) W. J. Bailey and E. W. Cummins, J. Am. Chem. Soc., 1954, 76, 1932;
9. c) W. J. Bailey and E. W. Cummins, J. Am. Chem. Soc., 1954, 76, 1936;
10. d) W. J. Bailey and E. W. Cummins, J. Am. Chem. Soc., 1954, 76, 1940;
11. e) W. Davis and F. C. James, J. Chem. Soc., 1954, 15;
12. f) M. Prochazka, Collect. Czech. Chem. Commun., 1965, 30, 1158;
13. g) S. E. Reiter, L. C. Dunn, and K. N. Houk, J. Am. Chem. Soc., 1977, 99, 4199;
14. h) D. Copland, D. Leaver, and W. B. Menzies, Tetrahedron Lett., 1977, 639;
15. i) R. T. Patterson, Diss. Abstr. Int., 1980, 41, 204-B;
16. j) J. Becker, C. Wentrup, E. Katz, and K.-P. Zeller, J. Am. Chem. Soc., 1980, 102, 5110;
17. k) K.-P. Zeller, Z. Naturforsch., 1981, 36b, 858;
18. l) F. M. Albini, M. P. Ceva, A. Mascherpa, E. Albini, and P. Caramella, Tetrahedron, 1982, 38, 3629;
19. m) T. MoIz, P. Konig, R. Goes, G. Gauglitz, and H. Meier, Chem. Ber., 1984, 117, 833;
20. n) H. Meier, T. Molz, and H. Z. Kolshorn, Z. Naturforsch., 1984, 39b, 915;
21. o) H. A. Bates, L. Smilowitz, and J. Lin, J. Org. Chem., 1985, 50, 899;
22. p) A. Wetzel and K.-P. Zeller, Z. Naturforsch., 1987, 42b, 903;
23. q) T.-s. Chou, S. C. Hung, and H.-H. Tso, J. Org. Chem., 1987, 52, 3394;
24. r) T.-s. Chou and M.-M. Chen, Heterocycles, 1987, 26, 2829;
25. s) T.-s. Chou and M.-M. Chen, J. Chin. Chem. Soc., 1988, 35, 373;
26. t) P. Muller and J.-P. Schaller, Helv. Chim. Acta, 1989, 72, 1608;
27. u) B. R. Dent and G. Gainsford, Aust. J. Chem., 1989, 42, 1307;
28. v) P. A. Frolov, D. F. Kushnarev, F. N. Iglamova, B. A. Bazhenov, and G. A. Kalabin, Neftekhimiya, 1990, 30, 556.
29. For metal carbonyl complex formation, see
30. a) Y. L. Chow, J. Fossey, and R. A. Perry, J. Chem. Soc., Chem. Commun., 1972, 501;
31. b) J. H. Eekhof, H. Hogeveen, R. M. Kellogg, and G. A. Sawatzky, J. Organometal. Chem., 1976, 111, 349;
32. c) R. Albrecht and E. Weiss, J. Organometal. Chem., 1990, 399, 163;
33. d) R. Albrecht and E. Weiss, J. Organometal. Chem., 1991, 413, 355;
34. e) F. Meier-Brocks, R. Albrecht, and E. Weiss, J. Organometal. Chem., 1992, 439, 65.
35. For theoretical study, see
36. a) L. Fortina and G. Montaudo, Gazz. Chim. Ital., 1960, 987;
37. b) P. W. Lert and C. Trindle, J. Am. Chem. Soc., 1971, 93, 6392;
38. c) F. de Jong and M. Janssen, J. Chem. Soc., Perkin Trans. 2, 1972, 572;
39. d) F. de Jong and M. Janssen, Rec. Trav. Chim. Pays-Bas, 1973, 92, 1073;
40. e) F. de Jong, A. J. Noorduin, M. T. Bouwman, and M. Janssen, Tetrahedron Lett., 1974, 1209;
41. f) I. Rozas, J. Phys. Org. Chem., 1992, 5, 74;
42. g) B. S. Jursic, J. Heterocycl. Chem., 1995, 32, 1445.
43. J. Nakayama, H. Nagasawa, Y. Sugihara, and A. Ishii, J. Am. Chem. Soc., 1997, 119, 9077.
44. W. Adam, L. Hadjiarapoglou, and A. Smerz, Chem. Ber., 1991, 124, 227.
45. For pereparation of isolable stable thiophene 1,1 -dioxides by oxidation of thiophenes with DMD, see Y. Miyahara and T. Inazu, Tetrahedron Lett., 1990, 31, 5955.
46. a) W. J. M. van Tiborg and R. Plomp, Rec. Trav. Chim. Pays-Bas, 1977, 96, 282;
47. b) J. Nakayama, Y. Sugihara, K. Terada, and E. L. Clennan, Tetrahedron Lett., 1990, 31, 4473.
48. A. Altomare, G. Cascarano, O. Giacovazzo, A. Guagliard, M. C. Burla, G. Polidori, and M. Camalli, J. Appl. Cryst., 1984, 27, 435.
49. P. R. Mallinson and K. W. Muir, J. Appl. Cryst., 1985, 28, 31.