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Abstract:

Aromatic and aliphatic aldehydes are transformed in 1,1-diacetates (acylals) in mild conditions, by a treatment with acetic anhydride and a Wells-Dawson acid (H6P2W18O62·24H 2O). gem-Diacetylation proceeds in Ac2O with a little as 1% mol Wells-Dawson acid at room temperature and under solventless conditions, obtaining very good to excellent yields (88-98%) of 1,1-diacetates (19 examples). Neither 4-dimethylaminobenzaldehyde nor ketones react under the same conditions. © 2003 Elsevier Science Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H 2O)
Autor:Romanelli, G.P.; Thomas, H.J.; Baronetti, G.T.; Autino, J.C.
Filiación:Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Calles 47 y 115, (1900) La Plata, Argentina
Ctro. de Invest. y D. en C. A., Departamento de Química, Univ. Nacional de La Plata-CONICET, Calle 47 No 257, (1900) La Plata, Argentina
Depto. de Ingenieria Quim., Universidad de Buenos Aires, Ciudad Universitaria, (1428) Buenos Aires, Argentina
Palabras clave:1,1-diacetate; Acylal; Aldehyde; Heteropolyacid; Protecting group; Wells-Dawson catalyst; 2,3 butanedione; 4 dimethylaminobenzaldehyde; acetic anhydride; acetoacetic acid derivative; acid; aldehyde; aliphatic compound; aromatic compound; ketone derivative; solvent; unclassified drug; Wells Dawson acid; acetylation; article; catalysis; gas liquid chromatography; room temperature; thin layer chromatography
Año:2003
Volumen:44
Número:6
Página de inicio:1301
Página de fin:1303
DOI: http://dx.doi.org/10.1016/S0040-4039(02)02817-4
Título revista:Tetrahedron Letters
Título revista abreviado:Tetrahedron Lett.
ISSN:00404039
CODEN:TELEA
CAS:2,3 butanedione, 431-03-8; 4 dimethylaminobenzaldehyde, 100-10-7, 28602-27-9; acetic anhydride, 108-24-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v44_n6_p1301_Romanelli

Referencias:

  • Greene, T.W., Wuts, P.G.M., (1991) Protection for the Carbonyl Group, Protective Groups in Organic Synthesis 2nd ed., p. 184. , New York: John Wiley
  • Pereira, C., Gigante, B., Marcelo-Curto, M.J., Carreyre, H., Pérot, G., Guisnet, M., (1995) Synthesis, pp. 1077-1078
  • Kochhar, K.S., Bal, B.S., Deshpande, R.P., Rajadhyaksha, S.N., Pinnick, H.W., (1983) J. Org. Chem., 48, pp. 1765-1767
  • Kumar, P., Hedge, V.R., Kumar, T.P., (1995) Tetrahedron Lett., 36, pp. 601-602. , and references cited therein
  • Gregory, M.J., (1970) J. Chem. Soc. B, pp. 1201-1207
  • Olah, G.H., Mehrotra, A.K., (1982) Synthesis, pp. 962-963
  • Jin, T.-S., Ma, Y.-R., Zhang, Z.-H., Li, T.-S., (1997) Synth. Commun., 27, pp. 3379-3383
  • Li, Y.-Q., (2000) Synth. Commun., 30, pp. 3913-3917
  • Deka, N., Kalita, D.J., Borah, R., Sarma, J.C., (1997) J. Org. Chem., 62, pp. 1563-1564
  • Joshi, M.V., Narasimhan, C.S., (1993) J. Catal., 141, pp. 308-310
  • Li, T.-S., Zhang, Z.-H., Gao, Y.-J., (1998) Synth. Commun., 28, pp. 4665-4672
  • Curini, M., Epifano, F., Marcotullio, M.C., Rosati, O., Nocchetti, M., (2002) Tetrahedron Lett., 43, pp. 2709-2711
  • Kozhevnikov, I.V., (1998) Chem. Rev., 98, pp. 171-198
  • Baronetti, G.T., Briand, L., Sedran, U., Thomas, H., (1998) Appl. Catal. A, 172, pp. 265-272
  • Romanelli, G.P., Baronetti, G., Thomas, H.J., Autino, J.C., (2002) Tetrahedron Lett., 43, pp. 7589-7591
  • Romanelli, G.P., Autino, J.C., Baronetti, G., Thomas, H., (2001) Molecules, 6, pp. 1006-1011
  • Romanelli, G.P., Vázquez, P.G., Pizzio, L.R., Cáceres, C.V., Blanco, M.N., Autino, J.C., Synth. Commun., , in press

Citas:

---------- APA ----------
Romanelli, G.P., Thomas, H.J., Baronetti, G.T. & Autino, J.C. (2003) . Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H 2O). Tetrahedron Letters, 44(6), 1301-1303.
http://dx.doi.org/10.1016/S0040-4039(02)02817-4
---------- CHICAGO ----------
Romanelli, G.P., Thomas, H.J., Baronetti, G.T., Autino, J.C. "Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H 2O)" . Tetrahedron Letters 44, no. 6 (2003) : 1301-1303.
http://dx.doi.org/10.1016/S0040-4039(02)02817-4
---------- MLA ----------
Romanelli, G.P., Thomas, H.J., Baronetti, G.T., Autino, J.C. "Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H 2O)" . Tetrahedron Letters, vol. 44, no. 6, 2003, pp. 1301-1303.
http://dx.doi.org/10.1016/S0040-4039(02)02817-4
---------- VANCOUVER ----------
Romanelli, G.P., Thomas, H.J., Baronetti, G.T., Autino, J.C. Solvent-free catalytic preparation of 1,1-diacetates from aldehydes using a Wells-Dawson acid (H6P2W18O62·24H 2O). Tetrahedron Lett. 2003;44(6):1301-1303.
http://dx.doi.org/10.1016/S0040-4039(02)02817-4