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Abstract:

Studies of the reaction of lithium dicyclohexylamide with N,N- dibutylformamide, 1-formylpiperidine, and 4-formylmorpholine indicate that the equilibria resulting from these compounds are shifted toward the formation of an adduct, which quickly collapses to dicyclohexylamine and the lithiated carbamoyl anion derived from the initial disubstituted formamide. Further reactions of the lithium carbamoyl lead to a new adduct where a lithiated carbon is bounded to N, O, and a carbonyl functionality. The 13C NMR analysis of the reaction mixtures showed the presence of similar intermediates in all cases: adducts of this type have not been reported before. These dilithiated intermediates were trapped with methyl iodide giving the corresponding doubly methylated derivatives. Isolation of substituted glyoxylamides and quantitative determination of the products yields constitute further evidence of the whole reaction scheme proposed.

Registro:

Documento: Artículo
Título:New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2)
Autor:Nudelman, N.S.; García Liñares, G.E.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, P. 3, 1428 Buenos Aires, Argentina
Palabras clave:1 formylpiperidine; 4 formylmorpholine; formamide derivative; glyoxylamide; lithium dicyclohexylamide; n,n dibutylformamide; unclassified drug; article; carbon nuclear magnetic resonance; chemical binding; chemical reaction kinetics; organic chemistry; quantitative assay; reaction analysis; structure analysis
Año:2000
Volumen:65
Número:6
Página de inicio:1629
Página de fin:1635
DOI: http://dx.doi.org/10.1021/jo9908445
Título revista:Journal of Organic Chemistry
Título revista abreviado:J. Org. Chem.
ISSN:00223263
CODEN:JOCEA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v65_n6_p1629_Nudelman

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Citas:

---------- APA ----------
Nudelman, N.S. & García Liñares, G.E. (2000) . New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2). Journal of Organic Chemistry, 65(6), 1629-1635.
http://dx.doi.org/10.1021/jo9908445
---------- CHICAGO ----------
Nudelman, N.S., García Liñares, G.E. "New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2)" . Journal of Organic Chemistry 65, no. 6 (2000) : 1629-1635.
http://dx.doi.org/10.1021/jo9908445
---------- MLA ----------
Nudelman, N.S., García Liñares, G.E. "New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2)" . Journal of Organic Chemistry, vol. 65, no. 6, 2000, pp. 1629-1635.
http://dx.doi.org/10.1021/jo9908445
---------- VANCOUVER ----------
Nudelman, N.S., García Liñares, G.E. New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2). J. Org. Chem. 2000;65(6):1629-1635.
http://dx.doi.org/10.1021/jo9908445