Mechanistic studies on the reactions of trimethylsilanide and trimethylstannylide ions with haloarenes in hexamethylphosphoramide

Journal of Organometallic Chemistry

Volumn 656, Issue 1-2, 2002, Pages 108-115

  Postigo, Al ^a   Vaillard, Santiago E ^a   Rossi, Roberto A ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

Hypervalent silicon; SRN1 reaction, HME reaction; Trimethylsilanide ions; Trimethylstannylide ions

Indexed keywords

AMMONIA; LIQUEFIED GASES; SILICON; SUBSTITUTION REACTIONS;

CHLOROARENES; HALOARENES; HEXAMETHYLPHOSPHORAMIDE; HYPERVALENT SILICON; MECHANISTIC STUDIES; NEGATIVE CHARGE; SI IONS; SRN1 REACTION, HME REACTION; TRIMETHYLSILANIDE ION; TRIMETHYLSTANNYLIDE ION;

IONS;

EID: 0013118464     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(02)01572-3     Document Type: Article

References (31)

1. Wursthorn, K.R., Kuivila, H.G., Smith, G.F., J. Am. Chem. Soc., 100, 1978, 2779.
2. Quintard, J.P., Hauvette-Frey, S., Pereyre, M., J. Organomet. Chem., 112, 1976, C11.
3. Quintard, J.P., Hauvette-Frey, S., Pereyre, M., J. Organomet. Chem., 159, 1978, 147.
4. Yammal, C.C., Podestá, J.C., Rossi, R.A., J. Org. Chem., 57, 1992, 5720.
5. Yammal, C.C., Podestá, J.C., Rossi, R.A., J. Organomet. Chem., 509, 1996, 1.
6. E.F. Córsico, R.A. Rossi, Synlett (2000) 227.
7. E.F. Córsico, R.A. Rossi, Synlett (2000) 230.
8. D. Wittenberg, H. Gilman, Quaterly Rev. (1960) 116.
9. Postigo, A., Rossi, R.A., Org. Lett., 8, 2001, 1197.
10. A. Postigo, S.E. Vaillard, R.A. Rossi, unpublished results.
11. Bunnett, J.F., Acc. Chem. Res., 11, 1978, 413.
12. It is known that 2,3-dehydrobenzotrifluoride, upon reaction with PhLi, affords 46% of the respective meta-substituted isomer. See R.W. Hoffmann, Dehydrobenzene and Cycloalkanes, Verlag Chemie. GmbH. Academic Press, 11 (1967) 106–107.
13. RN1 Mechanism; ACS Monograph 178; Washington, D.C., 1983.
14. RN1 Reaction. In: L.A. Paquette. and R. Bittman (Eds.), Organic Reactions, Wiley, New York, 1999; Vol. 54, pp. 1-271.
15. R.K. Norris, in: B.M. Trost (Ed.), Comprehensive Organic Synthesis, 4 (1991) 451.
16. R.A. Rossi, A.B Pierini, A.B. Peñéñory, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Functional Group, Wiley, Chichester, Suppl. D2, Ch. 24, 1995, p. 1395.
17. Meijs, G.F., Beckwith, A.L.J., J. Am. Chem. Soc., 108, 1986, 5890.
18. Beckwith, A.L.J., Meijs, G.F., J. Org. Chem., 52, 1987, 1922.
19. Beckwith, A.L.J., Palacios, S.M., J. Phys. Org. Chem., 4, 1991, 404.
20. Moerlein, S.M., J. Organomet. Chem., 319, 1987, 29.
21. Eaborn, C., Hornfeld, H.L., Walton, D.R.M., J. Organomet. Chem., 10, 1967, 529.
22. Smith, A., Adcock, W., Kitching, W., J. Am. Chem. Soc., 92, 1970, 6140.
23. Nishimura, J., Furukawa, J., Kawabata, N., J. Organomet. Chem., 29, 1971, 237.
24. Freeburger, M.E., Spialter, L., J. Am. Chem. Soc., 93, 1971, 1894.
25. Haubold, W., Herdtle, J., Gollinger, W., J. Organomet. Chem., 315, 1986, 1.
26. A.N. Abeywickrema, A.L.J. Beckwith, Tetrahedron Lett. (1986) 109.
27. Krotikov, Y.V., Zargorodnii, V.S., Petrov, A.A., Metallorg. Khim., 54, 1992, 960.
28. Krotikov, Y.V., Zargorodnii, V.S., Petrov, A.A., Chem. Abstr., 118, 1993, 81060z.
29. Bogolepova, Y.V., Vygoeskaya, I.V., Kliger, G.A., Loktev, S.M., Nafte Khimiya, 31, 1991, 805.
30. Bogolepova, Y.V., Vygoeskaya, I.V., Kliger, G.A., Loktev, S.M., Chem. Abstr., 116, 1992, 12827y.
31. J.P. Pillot, J. Dunogues, J. Geval, Eur. Polym. J. 25 (1989) 285.