Artículo
Nudelman, N.S.; Mendiara, S. "Reactions of lithium with benzaldehyde in solution" (1997) Journal of Physical Organic Chemistry. 10(4):233-241
Consulte la política de Acceso Abierto del editor
Abstract:
Benzaldehyde in THF reacts with lithium metal to give the expected reduction product, benzyl alcohol, plus benzoin and benzyl as minor products. The kinetics of the overall reaction as well as the partial rate coefficients of the several steps have been determined under various reaction conditions. It was found that adsorption on the surface and electron transfer from the lithium to benzaldehyde are the slow steps. The experimental results show interesting surface effects, and evidence for significant radical intermediates, which were characterized by their epr spectra and trapping experiments, results useful to gain insight into the mechanisms of these and other related reactions. © 1997 by John Wiley & Sons, Ltd.
Registro:
| Documento: | Artículo |
| Título: | Reactions of lithium with benzaldehyde in solution |
| Autor: | Nudelman, N.S.; Mendiara, S. |
| Filiación: | Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina Departamento de Quimica, Facultad de Ciencias Exactas, Universidad de Mar del Plata, Mar del Plata, Argentina |
| Palabras clave: | Benzoyl radical; Coupling of radicals; Electron transfer; Radical anions; Reactions in the double layer; Surface catalysis; Surface effects |
| Año: | 1997 |
| Volumen: | 10 |
| Número: | 4 |
| Página de inicio: | 233 |
| Página de fin: | 241 |
| DOI: | http://dx.doi.org/10.1002/(SICI)1099-1395(199704)10:4<233::AID-POC899>3.0.CO;2-Z |
| Título revista: | Journal of Physical Organic Chemistry |
| Título revista abreviado: | J Phys Org Chem |
| ISSN: | 08943230 |
| CODEN: | JPOCE |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_08943230_v10_n4_p233_Nudelman |
Referencias:
- Eberson, L., (1992) New J. Chem., 16, p. 151
- Eberson, L., (1987) Electron Transfer Reactions in Organic Chemistry, , Springer, Berlin
- Fox, M.A., (1992) Chem. Rev., 92, p. 365
- Fox, M.A., Chanon, M., (1988) Photoinduced Electron Transfer, , Elsevier, Amsterdam
- Saveant, J.M., (1992) New J. Chem., 16, p. 131
- Bolton, J.R., Mataga, N., McLendon, G., (1991) Electron Transfer in Inorganic, Organic, and Biologial Systems, Advances in Chemistry Series, 228. , American Chemical Society, Washington, DC
- Furstner, A., Csuk, R., Rohre, C., Weidmann, H., (1988) J. Chem. Soc., Perkin Trans, 1, p. 1729
- March, J., (1992) Advanced Organic Chemistry, 4th Ed., , Chapt. 19, Wiley, New York
- Holton, D.M., Edwards, P.P., Johnson, D.C., Page, C.J., McFarlane, W., Wood, B., (1987) J. Am. Chem. Soc., 109, p. 6499
- Garst, J.F., Swift, B.L., Smith, D.W., (1989) J. Am. Chem. Soc., 111, p. 241
- Wittcoff, H.A., Reuben, B.G., (1992) Industrial Organic Chemicals Perspective. Part I: Raw Materials and Manufacture, , Wiley, New York
- Liu, Z.T., Zhang, B.J., (1994) J. Mol. Catal., 94, p. 255
- Nudelman, N.S., (1989) The Chemistry of Double Bonded Functional Groups, , edited by S. Patai and Z. Rappoport, chap. 29. Wiley, Chichester
- Nudelman, N.S., Doctorovich, F., (1994) Tetrahedron, 50, p. 4651
- Ingold, K., Neville, A., Brown, C., Rayner, D., Lusztyk, J., (1991) J. Am. Chem. Soc., 113, p. 1869
- Nudelman, N.S., Lewkowicz, E.S., Furlong, J.P.J., (1993) J. Org. Chem., 58, p. 1847
- Nudelman, N.S., Lewkowicz, E.S., Perez, D.G., (1990) Synthesis, p. 917
- Perez, D.G., Nudelman, N.S., (1988) J. Org. Chem., 53, p. 408
- Masnovi, J., Maticic, J., (1988) J. Am. Chem. Soc., 110, p. 5189
- Atherton, S.J., (1984) J. Phys. Chem., 88, p. 2840
- Saito, Y., Ikehira, H., Kasatani, R., Watanabe, M., Matsuura, T., (1986) J. Am. Chem. Soc., 108, p. 5190
- Masnovi, J.M., Samsel, E.G., Bullok, R.M., (1989) J. Chem. Soc., Chem. Commun., p. 1044
- Ashby, E.C., Park, B., Patil, G.S., Gurumurthy, R., (1993) J. Org. Chem., 58, p. 424
- Scott, L.T., Carlin, K.J., Schulz, T.H., (1978) Tetrahedron Lett., p. 4637
- Doctorovich, F., Nudelman, N.S., (1990) Magn. Reson Chem., 28, p. 576
- Nudelman, N.S., Doctorovich, F., Amorin, G., (1990) Tetrahedron Lett., 31, p. 2533
- Kowalski, C., Creary, C., Rollin, A.J., Burke, M.C., (1978) J. Org. Chem., 43, p. 3101
- Newcomb, M., Burchill, M.T., (1984) J. Am. Chem.Soc., 106, p. 2450
- Newcomb, M., Burchill, M.T., Deeb, T.M., (1988) J. Am. Chem. Soc., 110, p. 6528
- Garst, J.F., Swift, B.L., Smith, D.W., (1989) J. Am. Chem. Soc., 111, p. 234
- Barber, J.J., Whitesides, G.M., (1980) J. Am. Chem. Soc., 102, p. 239
- Nudelman, N.S., Doctorovich, F., (1984) J. Chem. Soc., Perkin Trans. 2, p. 1233
- Rice, S.A., (1985) Comprehensive Chemical Kinetics, 25. , edited by C. H. Bamford, C. H. Tipper and R. G. Compton, Elsevier, Amsterdam
- Nuzzo, R.G., Dubois, L.H., (1986) J. Am. Chem. Soc., 108, p. 2881
- Garst, J.F., Deutch, J.M., Whitesides, G.M., (1986) J. Am. Chem. Soc., 108, p. 2490
- Bard, A.J., Faulkner, L.R., (1980) Electrochemical Methods, p. 514. , Wiley, New York
- Vitale, A.A., Doctorovich, F., Nudelman, N.S., (1980) J. Organomet. Chem., 332, p. 9
- Nudelman, N.S., Vitale, A.A., (1981) J. Org. Chem., 46, p. 4625
- Nudelman, N.S., Vitale, A.A., (1983) J. Organomet. Chem., 241, p. 143
- Nudelman, N.S., Outumuro, P., (1982) J. Org. Chem., 42, p. 4347
- Shriver, D.F., (1989) The Manipulation of Air Sensitive Compounds, , Wiley, New York
Citas:
---------- APA ----------
Nudelman, N.S. & Mendiara, S. (1997) . Reactions of lithium with benzaldehyde in solution. Journal of Physical Organic Chemistry, 10(4), 233-241.http://dx.doi.org/10.1002/(SICI)1099-1395(199704)10:4<233::AID-POC899>3.0.CO;2-Z
---------- CHICAGO ----------
Nudelman, N.S., Mendiara, S. "Reactions of lithium with benzaldehyde in solution" . Journal of Physical Organic Chemistry 10, no. 4 (1997) : 233-241.http://dx.doi.org/10.1002/(SICI)1099-1395(199704)10:4<233::AID-POC899>3.0.CO;2-Z
---------- MLA ----------
Nudelman, N.S., Mendiara, S. "Reactions of lithium with benzaldehyde in solution" . Journal of Physical Organic Chemistry, vol. 10, no. 4, 1997, pp. 233-241.http://dx.doi.org/10.1002/(SICI)1099-1395(199704)10:4<233::AID-POC899>3.0.CO;2-Z
---------- VANCOUVER ----------
Nudelman, N.S., Mendiara, S. Reactions of lithium with benzaldehyde in solution. J Phys Org Chem. 1997;10(4):233-241.http://dx.doi.org/10.1002/(SICI)1099-1395(199704)10:4<233::AID-POC899>3.0.CO;2-Z
