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Abstract:

The reaction of lithium dialkylamides 1 (dialkyl = dibutyl, dipentyl, dicyclohexyl, 3-oxapentamethylene, and isopropyl cyclohexyl) with carbon monoxide was examined under several reaction conditions. It is shown that the corresponding lithium carbamoyl is the first intermediate and its further reactions can lead to dialkylformamides 2, dialkylglyoxylamides 3, or tetraalkylhydroxymalonamides 4. Dialkylamides were previously assumed to come from hydrolysis of lithium carbamoyls, and these represent an unexplained “island of stability” among the area of acyl anions. Evidence is given that casts doubts on this assumption and suggests that 2 comes from the cleavage of lithium tetraalkylurea dianion. The yields of 2, 3, or 4 obtained by this one-step, rapid procedure are much higher than those afforded by the usual several steps methods of preparation, especially for compounds 3 and 4. Tetraalkylureas, tetraalkyloxalamines, or tetraalkylketomalonamides can be obtained in good yield by the same general procedure, followed by treatment of the reaction mixture with oxygen after the carbon monoxide absorption has ceased and before the regular workup. © 1988, American Chemical Society. All rights reserved.

Registro:

Documento: Artículo
Título:Carbon-Carbon Bond Formation through the Carbonylation of Lithium Dialkylamides. One-Pot Synthesis of N-Alkyl-Substituted Formamides, Glyoxylamides, and Hydroxymalonamides
Autor:Pérez, D.G.; Sbarbati Nudelman, N.
Filiación:Depto. Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pab. II, P.3 Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1988
Volumen:53
Número:2
Página de inicio:408
Página de fin:413
DOI: http://dx.doi.org/10.1021/jo00237a033
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v53_n2_p408_Perez

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Citas:

---------- APA ----------
Pérez, D.G. & Sbarbati Nudelman, N. (1988) . Carbon-Carbon Bond Formation through the Carbonylation of Lithium Dialkylamides. One-Pot Synthesis of N-Alkyl-Substituted Formamides, Glyoxylamides, and Hydroxymalonamides. Journal of Organic Chemistry, 53(2), 408-413.
http://dx.doi.org/10.1021/jo00237a033
---------- CHICAGO ----------
Pérez, D.G., Sbarbati Nudelman, N. "Carbon-Carbon Bond Formation through the Carbonylation of Lithium Dialkylamides. One-Pot Synthesis of N-Alkyl-Substituted Formamides, Glyoxylamides, and Hydroxymalonamides" . Journal of Organic Chemistry 53, no. 2 (1988) : 408-413.
http://dx.doi.org/10.1021/jo00237a033
---------- MLA ----------
Pérez, D.G., Sbarbati Nudelman, N. "Carbon-Carbon Bond Formation through the Carbonylation of Lithium Dialkylamides. One-Pot Synthesis of N-Alkyl-Substituted Formamides, Glyoxylamides, and Hydroxymalonamides" . Journal of Organic Chemistry, vol. 53, no. 2, 1988, pp. 408-413.
http://dx.doi.org/10.1021/jo00237a033
---------- VANCOUVER ----------
Pérez, D.G., Sbarbati Nudelman, N. Carbon-Carbon Bond Formation through the Carbonylation of Lithium Dialkylamides. One-Pot Synthesis of N-Alkyl-Substituted Formamides, Glyoxylamides, and Hydroxymalonamides. J. Org. Chem. 1988;53(2):408-413.
http://dx.doi.org/10.1021/jo00237a033