One-pot preparation of isomeric acetyl- and 2,2,2-trifluoroacetyl-azidothiophenes by selective bifunctionalization of dibromothiophenes via halogen-lithio exchange

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 10, 1996, Pages 963-964

  Spagnolo, Piero ^a   Zanirato, Paolo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042505258     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960000963     Document Type: Article

References (23)

1. For information about the chemistry of organic azides (and nitrenes) the reader is referred to the following useful books and reviews: E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297;
2. E. F. V. Scriven, Azides and Nitrenes: Reactivity and Utility, Academic Press, New York, 1984;
3. L. K. Dyall, in The Chemistry of Functional Groups, Supplement D, ed. S. Patai and Z. Rappoport, Wiley, Chichester, 1983, vol. 1;
4. S. Patai, The Chemistry of the Azido Group, Interscience Publishers, London, 1971;
5. W. Lwowski, Nitrenes, Interscience Publishers, New York, 1970.
6. P. Spagnolo and P. Zanirato, J. Org. Chem., 1978, 43, 3539.
7. S. Gronowitz, C. Westerlund and A.-B. Hornfeldt, Acta Chem. Scand., Ser. B, 1975, 29, 224.
8. A. Degl'Innocenti, M. Funicello, P. Scafato, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1995, 2141.
9. M. Funicello, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1990, 2971.
10. D. Spinelli and P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1993, 1129.
11. S. Gronowitz and P. Zanirato, J. Chem. Soc., Perkin Trans. 2, 1994, 1815.
12. P. J. Newcombe and R. K. Norris, Tetrahedron Lett., 1981, 22, 699;
13. B. J. Barnes, P. J. Newcombe and R. K. Norris, Aust. J. Chem., 1983, 36, 963.
14. G. L'abbé, L. K. Dyall, K. Meersman and W. Dehaen, J. Chem. Soc., Perkin Trans. 2, 1994, 2401.
15. D. Davies, P. Spagnolo and P. Zanirato, J. Chem. Soc., Perkin Trans. 1, 1995, 613.
16. R. K. Norris, Aminothiophenes and Their Derivatives, in The Chemistry of Heterocyclic Compounds, ed. S. Gronowitz, 1991, vol. 44, ch. 5, p. 631.
17. S. Gronowitz, P. Spagnolo, P. Zanirato, J. Org. Chem., 1982, 47, 3177;
18. J. Becher, K. Pluta, N. Krake, K. Brondum, N. J. Christensen and M. V. Vinader, Synthesis, 1988, 530.
19. L. Benati, P. C. Montevecchi, D. Nanni, P. Spagnolo and M. Volta, Tetrahedron Lett., 1995, 36, 7313.
20. B. J. Wakefield, Organolithium methods, Academic Press, London, 1988.
21. U. Michael and S. Gronowitz, Acta Chem. Scand., 1968, 22, 1353,
22. W. S. Di Menna, Tetrahedron Lett., 1980, 21, 2129.
23. C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165.