A New Organosilicon Synthon, 2,3,5,6-Tetrakis(trimethylsilyl)-1,3-cyclohexadiene. Versatile Polyfunctionalization of o-Dichlorobenzene

Organometallics

Volumn 1, Issue 11, 1982, Pages 1525-1528

  Dunoguès, Jacques ^a   N'Gabe, Denis ^a   Laguerre, Michel ^a   Duffaut, Norbert ^a   Calas, Raymond ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845554333     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om00071a024     Document Type: Article

References (22)

1. R. Calas and J. Dunoguès, J. Organomet. Chem. Libr., 2, 277 (1976) and references therein;
2. M. Laguerre, J. Dunogues, R. Calas, and N. Duffaut, J. Organomet. Chem., 112, 49 (1976);
3. M. Laguerre, G. Félix, J. Dunoguès, and R. Calas, J. Org. Chem., 44, 4275 (1979);
4. Tetrahedron Lett., 22, 1227 (1981).
5. H. Clark, A. F. Gordon, C. W. Young, and M. J. Hunter, J. Am. Chem. Soc., 73, 3798 (1951);
6. C. Eaborn, K. L. Laura, and D. R. M. Walton, J. Chem. Soc. 1198 (1964);
7. C. Eaborn, and D. R. M. Walton, J. Chem. Soc. B 15 (1969).
8. P. Bourgeois and R. Calas, J. Organomet. Chem., 84, 16 (1975).
9. J. Dunoguès, E. Jousseaume, and R. Calas, J. Organomet. Chem., 71, 377 (1974).
10. T. Brennan and H. Gilman, J. Organomet. Chem., 12, 291 (1968).
11. H. Bock and H. Seidl, J. Organomet. Chem., 13, 87 (1968).
12. J.-P. Pillot, J. Dunoguès, and R. Calas, Bull. Soc. Chim. Fr., 2143 (1975);
13. Synth. Commun., 395 (1979).
14. G. A. Olah, S. C. Narang, B. G. B. Gupta, and R. Malhotra, J. Org. Chem., 44, 1247 (1979).
15. D. S. Pratt and G. A. Perkins, J. Am. Chem. Soc., 40, 221 (1918).
16. D. Seyferth and D. A. White, J. Am. Chem. Soc., 94, 3132 (1972). High yields are observed from a few millimoles of XIII as reported by these authors but from 0.1 mol of XIII the meta derivative XIV was formed in 55–60% yields.
17. G. Félix, F. Pisciotti, J. Dunoguès, and R. Calas, Angew. Chem., 89, 502 (1977);
18. Angew. Chem., Int. Ed. Engl. 16, 488 (1977);
19. Angew. Chem., Int. Ed. Engl., 18, 402 (1979).
20. For previous studies, see the review of C. Eaborn, J. Organomet. Chem., 100, 43 (1975).
21. J. A. Zapp, Jr., Science (Washington, D.C.), 190 (1975).
22. J. Dunoguès, J.-P. Pillot, and R. Calas, C. R. Hebd. Seances Acad. Sci., Ser. C, 278, 467 (1974).