Clay-catalyzed thioalkylation of thiophenes and benzo[b]thiophenes

Phosphorus, Sulfur and Silicon and Related Elements

Volumn 114, Issue 1-4, 1996, Pages 99-108

  Clark, Peter D ^a   Mesher, Shaun T E ^a   Primak, Alex ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

Benzo b thiophene; Clayzic; K10; Thioalkylation; Thiophene

Indexed keywords

EID: 0345984963     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509608046415     Document Type: Article

References (37)

1. P. Shu, L. Chiang, T. Emge, D. Holt, T. Kistenmacher, M. Lee, J. Stokes, T. Poehler, A. Bloch and D. Cowan, J. Chem. Soc., Chem. Commun., 920-921 (1981).
2. K. Kobayashi, Chem. Lett., 1423-1424 (1985).
3. E. M. Engler, V. V. Patel, J. R. Andersen, R. R. Schumaker and A. A. Fukushima, J. Am. Chem. Soc., 100, 3769-3776 (1978).
4. K. Lerstrup, M. Lee, D. Cowan and T. Kistenmacher, Mol. Cryst. Liq. Cryst., 120, 295-298 (1985).
5. L.-Y. Chiang, P. Shu, D. Holt and D. Cowan, J. Org. Chem., 48, 4713-4717 (1983).
6. S. Gronowitz, M. Temciuc and A.-B. Hörnfeldt, J. Hetocycl. Chem., 30, 1111-1116 (1993).
7. K. I. Sadykhov, M. M. Slidov and S. M. Aliev, Zh. Org. Khim., 19, 1747 (1983).
8. S. Gronowitz, P. Moses, A.-B. Hörnfeldt and R. Håkansson, Arkiv Kemi, 17, 165 (1961).
9. S. Gronowitz and U. Rosén, Chem. Scr., 1, 33 (1971).
10. C. M. Camaggi, L. Lunazzi and G. Piacucci, J. Chem. Soc., Perkin Trans. 2, 1491 (1973).
11. A. P. Yakubov, N. V. Grigoreva and L. I. Belenkii, Zh. Org. Khim., 14, 641 (1978); J. Org. Chem. USSR., 14, 593 (1978).
12. A. P. Yakubov, N. V. Grigoreva and L. I. Belenkii, Zh. Org. Khim., 14, 641 (1978); J. Org. Chem. USSR., 14, 593 (1978).
13. R. Gompper, E. Kutter and W. Töpfl, Liebigs Ann. Chem., 659, 90 (1962).
14. K. A. Jensen and L. Henriksen, Acta Chem. Scand., 22, 1107 (1968).
15. L. Henriksen and H. Autrup, Acta Chem. Scand., 26, 3342 (1972).
16. W.-D. Rudolf, J. Köditz, A. Tersakian and S. K. Chatterjee, Liebigs Ann. Chem., 387 (1992).
17. E. J. Smutny, J. Am. Chem. Soc., 91, 208 (1962).
18. P. Netchitailo, B. Decroix, J. Morel and P. Pastour, J. Heterocycl. Chem., 15, 337-342 (1978).
19. P. D. Clark, A. Kirk and R. A. Kydd, Cat. Lett., 25, 163-168 (1994).
20. R. Taylor, "Electrophilic Substitution of Thiophene and Its Derivatives in Advances in Heterocyclic Compounds," Thiophene and Its Derivatives, Part II, S. Gronowitz, ed., Chap. 1, Wiley, New York, 1986.
21. P. D. Clark and S. T. E. Mesher, Phosphorus, Sulfur, and Silicon, 105, 157-162 (1995).
22. P. D. Clark, A. Kirk and J. G. K. Yee, J. Org. Chem., 60, 1936-1938 (1995).
23. J. H. Clark, A. P. Kybett, D. J. Macquarrie, S. J. Barlow and P. Landon, J. Chem. Soc., Chem. Commun., 1353-1354 (1989).
24. C. N. Rhodes, M. Franks, G. M. B. Parkes and D. R. Brown, J. Chem. Soc. Chem. Commun., 804-807 (1991).
25. J. H. Clark, S. R. Cullen, S. J. Barlow and T. W. Bastock, J. Chem. Soc., Perkin Trans. 2, 1117-1130 (1994).
26. A. Cornélis and P. Laszlo, Synlett, 155-161 (1994).
27. K. Smith and G. M. Pollaud, J. Chem. Soc., Perkin Trans. 1, 3519-3520 (1994).
28. J. J. Vanden Eynde, A. Mayence and Y. Van Haverbeke, Tetrahedron Lett., 36, 3133-3136 (1995).
29. L. I. Belenkii, A. P. Yakubov and Y. L. Goldfarb, Zh. Org. Khim., 11, 424-431 (1975).
30. A. P. Yakubov, N. V. Grigoreva and L. I. Belenkii, Zh. Org. Khim., 14, 641-650 (1978).
31. B. Iddon and R. M. Scrowston, Adv. Heterocyclic Chem., 11, 177 (1970).
32. R. M. Scrowston, Adv. Heterocyclic Chem., 29, 171 (1981).
33. R. A. Aitken, D. P. Armstrong and S. T. E. Mesher, Tetrahedron Lett., 35, 6143 (1994).
34. M. Parvez, S. T. E. Mesher and P. D. Clark, Acta. Cryst., C, 51, in press (1995).
35. M. Parvez, S. T. E. Mesher and P. D. Clark, Acta. Cryst., C, 51, in press (1995).
36. Y. L. Goldfarb, M. A. Kalik and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Ser. Khim, 8, 1769-1775 (1969); CA: 72:3302x.
37. Y. L. Goldfarb, M. A. Kalik and M. L. Kirmalova, Izv. Akad. Nauk SSSR, Ser. Khim, 8, 1769-1775 (1969); CA: 72:3302x.