Synthesis of New Functional Acenaphthylene Derivatives. 2. Regioselective Electrophilic Substitution of Silylated Acenaphthenes and Acenaphthylenes

Journal of Organic Chemistry

Volumn 47, Issue 8, 1982, Pages 1423-1427

  Félix, Guy ^a   Laguerre, Michel ^a   Dunoguès, Jacques ^a   Calas, Raymond ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005125922     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00347a008     Document Type: Article

References (43)

1. M. Laguerre, G. Félix, J. Dunoguès and R. Calas, J. Org. Chem., 44, 4275 (1979).
2. R. E. Dessy and S. A. Kandil, J. Org. Chem., 30, 3857 (1965);
3. M. P. Cava, K. E. Merkel, and R. H. Schlessinger, Tetrahedron, 21, 3059 (1965);
4. K. Rasheed, Tetrahedron, 22, 2957 (1966);
5. T. S. Cantrel and H. Shechter, J. Org. Chem., 33, 114 (1968);
6. G. P. Petrenko, N. S. Shepetukha, V. G. Usachenko, and E. N. Tel'nyuk, Zh. Org. Khim., 6, 1754 (1970);
7. V. G. Usachenko and G. P. Petrenko, Zh. Org. Khim., 7, 1489 (1971);
8. S. T. Weintraub and B. F. Plummer, J. Org. Chem., 36, 361 (1971);
9. M. P. Hadnall, Ph.D. Thesis, University of North Carolina, 1972;
10. R. Galante, Thèse de Spécialité, University of Bordeaux, 1973;
11. G. Dumartin, Thèse de Spécialité University of Bordeaux, 1973;
12. R. Lapouyade, R. Koussini, and J. C. Rayez, J. Chem. Soc., Chem. Commun., 676 (1975);
13. A. Castellan, G. Dumartin, R. Galante, and H. Bouas-Laurent, Bull. Soc. Chim. Fr., 217 (1976).
14. D. A. Herold and R. D. Rieke, J. Org. Chem., 44, 1359 (1979).
15. First reports concerning functionalization of vinylsilanes by electrophilic substitution of the silyl group were those of R. Calas, P. Bourgeois, N. Duffaut C. R. Hebd. Seances Acad. Sci., Ser. C, 263C, 243 (1966) (sulfonation)
16. and J.-P. Pillot, J. Dunoguès, and R. Calas, C. R. Hebd. Seances Acad. Sci., Ser. C; 278C, 789 (1974) (acetylation).
17. For a good review see T. H. Chan and I. Fleming, Synthesis, 761 (1979).
18. First reports concerning functionalization of arylsilanes were those of Eaborn et al. For good reviews see: C. Eabom, J. Organomet. Chem., 100, 43 (1975);
19. T. H. Chan and I. Fleming, Synthesis, 761 (1979);
20. D. Habisch and F. Effenberger, Synthesis, 841 (1979).
21. R. Calas and J. Dunoguès, J. Organomet. Chem. Libr., 2, 277 (1976).
22. J. Dunoguès, A. Ekouya, N. Duffaut, and R. Calas, J. Organomet. Chem., 87, 151 (1975).
23. M. Laguerre, J. Dunoguès, R. Calas, and N. Duffaut, J. Organomet. Chem., 112, 49 (1976).
24. R. G. Harvey and H. Cho, J. Am. Chem. Soc., 96, 2434 (1974).
25. M. Schmidt and H. Schmidbaur, Angew. Chem., 70, 469 (1958).
26. N. Duffaut, R. Calas, and J. Dunoguès, Bull. Soc. Chim. Fr., 512 (1963).
27. P. Bourgeois and R. Calas, J. Organomet. Chem., 84, 16 (1975).
28. P. Bourgeois and N. Duffaut, Bull. Soc. Chim. Fr., 195 (1979).
29. H. Cerfontain, Z. R. H. Schaasberg-Nienhais, J. Chem. Soc., Perkin Trans. 2 989 (1974).
30. L. F. Fieser and E. B. Hershberg, J. Am. Chem. Soc., 61, 1272 (1939);
31. D. Nightingale, H. E. Ungnade and H. E. French, J. Am. Chem. Soc., 67, 1262 (1945);
32. H. E. Nurnsten and A. T. Peters, J. Chem. Soc., 729 (1950).
33. G. E. O'Boyle, L. J. Scott, and B. F. Plummer, J. Org. Chem., 44, 514 (1979).
34. F. Sachs and G. Mosebach, Chem. Ber., 43, 2473 (1910);
35. Y. Ogata and I. Urasaki, J. Chem. Soc. C, 1689 (1970).
36. M. Grignon-Dubois, J.-P. Pillot, J. Dunogues, N. Duffaut, R. Calas, and B. Henner, J. Organomet. Chem., 124, 135 (1977).
37. G. Félix, J. Dunoguès, F. Pisciotti, and R. Calas, Angew. Chem., Int. Ed. Engl., 16, 488 (1977).
38. G. Félix, J. Dunoguès, and R. Calas, Angew. Chem., Int. Ed. Engl., 18, 402 (1979).
39. L. D. Hayward and I. G. Csiznadia, Tetrahedron, 19, 2111 (1963);
40. B. M. Trost, J. Am. Chem. Soc., 88, 853 (1966).
41. M. Laguerre, J. Dunoguès, and R. Calas, Tetrahedron Lett., 22, 1227 (1981).
42. G. Félix, M. Laguerre, J. Dunoguès, and R. Calas, J. Chem. Res., 236 (1980).
43. V. D. Lyashchenko, T. A. Sokolova, and V. V. Selinskii, J. Gen. Chem. USSR (Engl. Transi.), 11, 1001 (1941).