Artículo
Di Chenna, P.H.; André Ferrara; Ghini, A.A.; Burton, G. "Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides" (2002) Journal of the Chemical Society. Perkin Transactions 1. 2(2):227-231
Estamos trabajando para incorporar este artículo al repositorio
Consulte la política de Acceso Abierto del editor
Abstract:
Cyclopropyl ketones are converted into their hydrazones which react with mercury(II) oxide and mercury(II) acetate to give α-(acetoxymercurio)alkyl acetates. These are reducedin situ to the corresponding α-acetoxyalkylmercury(II) hydrides which rearrange spontaneously with cleavage of the cyclopropane ring. The procedure is used to obtain D-homo- and 17(13→18)-abeo-pregnanes.
Registro:
| Documento: | Artículo |
| Título: | Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides |
| Autor: | Di Chenna, P.H.; André Ferrara; Ghini, A.A.; Burton, G. |
| Filiación: | Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina |
| Palabras clave: | Chemical bonds; Conformations; Hydrides; Hydrolysis; Mercury compounds; Molecular structure; Stereochemistry; Cyclopropane bonds; Ketones |
| Año: | 2002 |
| Volumen: | 2 |
| Número: | 2 |
| Página de inicio: | 227 |
| Página de fin: | 231 |
| Título revista: | Journal of the Chemical Society. Perkin Transactions 1 |
| Título revista abreviado: | J Chem Soc Perkin Trans 1 |
| ISSN: | 14727781 |
| CODEN: | JCPRB |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v2_n2_p227_DiChenna |
Referencias:
- Ferrara, A., Burton, G., (1996) Tetrahedron Lett., 37, p. 929
- Ferrara, A., Benedetti, M.O.V., Ghini, A.A., Burton, G., (1993) J. Chem. Res. (S), p. 276
- Kantorowski, E.J., Eisenberg, S.W.E., Fink, W.H., Kurth, M.J., (1999) J. Org. Chem., 64, p. 570
- Dauben, W.G., Deviny, E.J., (1966) J. Org. Chem., 31, p. 3794
- Dauben, W.G., Wolf, R.E., (1970) J. Org. Chem., 35, p. 374
- Pereyre, M., Godet, J.Y., (1970) Tetrahedron Lett., p. 3653
- Pereyre, M., Quintard, J.P., (1981) Pure Appl. Chem., 53, p. 2401
- Kulicke, K.J., Giese, B., (1990) Synlett, p. 91
- Batey, R.A., Motherwell, W.B., (1991) Tetrahedron Lett., 32, p. 6211
- Giese, B., (1985) Angew. Chem., Int. Ed. Engl., 24, p. 553
- Giese, B., Erfort, U., (1983) Chem. Ber., 116, p. 1240
- Giese, B., (1986) Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, , Pergamon Press, Oxford, ch. 3
- Curran, D., (1991) Comprehensive Organic Synthesis, 4, p. 715. , ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford
- Holton, T.L., Shecheter, H., (1995) J. Org. Chem., 60, p. 4725
- Barton, D.H.R., McGhie, J.F., Balton, P.L., (1970) J. Chem. Soc. C, p. 1033
- Heusler, K., Kalvoda, J., Weiland, P., Wettstein, A., (1961) Helv. Chim. Acta, 44, p. 179
- Batey, R.A., Grice, P., Harling, J.D., Motherwell, W.B., Rzepa, H.S., (1992) J. Chem. Soc., Chem. Commun., p. 942
- Ingold, K.U., Walton, J.C., (1986) Acc. Chem. Res., 19, p. 72
- Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Pople, J.A., (1998) Gaussian 98 (Revision A.7), , Gaussian, Inc., Pittsburgh, PA
- Lee, P.H., Lee, B., Lee, J., Park, S.K., (1999) Tetrahedron Lett., 40, p. 3427
- Martinez, F.N., Schlegel, H.B., Newcomb, M., (1998) J. Org. Chem., 63, p. 3618
- Batey, R.A., Harling, J.D., Motherwell, W.B., (1992) Tetrahedron, 48, p. 8031
- Clive, D.L.J., Daigneault, S., (1991) J. Org. Chem., 56, p. 3801
- Corey, E.J., Chaykovsky, M., (1965) J. Am. Chem. Soc., 87, p. 1353
- Steinberg, N.G., Rasmusson, G.H., Reamer, R.A., (1979) J. Org. Chem., 44, p. 2294
Citas:
---------- APA ----------
Di Chenna, P.H., André Ferrara, Ghini, A.A. & Burton, G. (2002) . Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides. Journal of the Chemical Society. Perkin Transactions 1, 2(2), 227-231.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v2_n2_p227_DiChenna [ ]
---------- CHICAGO ----------
Di Chenna, P.H., André Ferrara, Ghini, A.A., Burton, G. "Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides" . Journal of the Chemical Society. Perkin Transactions 1 2, no. 2 (2002) : 227-231.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v2_n2_p227_DiChenna [ ]
---------- MLA ----------
Di Chenna, P.H., André Ferrara, Ghini, A.A., Burton, G. "Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides" . Journal of the Chemical Society. Perkin Transactions 1, vol. 2, no. 2, 2002, pp. 227-231.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v2_n2_p227_DiChenna [ ]
---------- VANCOUVER ----------
Di Chenna, P.H., André Ferrara, Ghini, A.A., Burton, G. Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides. J Chem Soc Perkin Trans 1. 2002;2(2):227-231.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14727781_v2_n2_p227_DiChenna [ ]
