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Abstract:

Studies of the reaction of lithium morpholide with N,N-dibutylformamide and 1-formyl-piperidine, respectively, indicate that in the complex equilibria resulting from these compounds the mixed diamino lithium alkoxides derived from morpholine and the corresponding amide (N,N-dibutylformamide or 1-formylpiperidine) are formed first. These intermediates then collapse to the lithium morpholide carbamoyl anion which reacts with morpholine to finally give the lithium dimorpholinemethoxide, which was detected by 13C NMR as well as independently synthesized.

Registro:

Documento: Artículo
Título:Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H)
Autor:Nudelman, N.S.; Schulz, H.; Liñares, G.G.; Bonatti, A.; Boche, G.
Filiación:Depto. de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Univ. de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Fachbereich Chemie, Philipps-Universitat Marburg, Marburg, Germany
Año:1998
Volumen:17
Número:2
Página de inicio:146
Página de fin:150
Título revista:Organometallics
Título revista abreviado:Organometallics
ISSN:02767333
CODEN:ORGND
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v17_n2_p146_Nudelman

Referencias:

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  • Nudelman, N.S., Lewkowicz, E.S., Furlong, J.J.P., (1993) J. Org. Chem., 58, p. 1847
  • Lucht, B.L., Collum, D.B., (1995) J. Am. Chem. Soc., 117, p. 9863
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  • Nudelman, N.S., Lewkowicz, E.S., Perez, D.G., (1990) Synthesis, 10, p. 917
  • Vedejs, E., Lee, N., (1995) J. Am. Chem. Soc., 117, p. 891. , and previous references
  • Boche, G., Langlotz, I., Marsch, M., Harms, K., Nudelman, N.S., (1992) Angew. Chem., Int. Ed. Engl., 104, p. 774
  • Pérez, D.G., Nudelman, N.S., (1988) J. Org. Chem., 53, p. 408
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  • Bitsi, G., Jenner, G., (1987) J. Organomet. Chem., 330 (3), p. 429
  • Nudelman, N.S., García Liñares, G., Schulz, H., (1995) Main Group Met. Chem., 78, p. 147
  • Nudelman, N.S., Doctorovich, F., García Liñares, G., Schulz, H., (1996) Gazz. Chim. Ital., 126, p. 19
  • Nudelman, N.S., García Liñares, G., (1996) An. Asoc. Quim. Argent., p. 619
  • Murugan, R., Scriven, E.F., Zhang, T.Y., PCT Int. Appl. WO 95 15,313, 1995; Chem. Abstr. 123, 143654k; Packman, T.W., Germain, A.L., Patel, R., Barras, J.R., Milne, D.J., PCT Int. Appl. WO 95 07,877, 1995; Chem. Abstr. 1995, 123, 55483y; Faraj, M.K., U.S. Patent 5,155,267, 1992; Chem. Abstr. 118, 80639h; Koeckritz, P., Liebscher, J., Schmidt, L., German (East) Patent DD 241,073, 1986; Chem. Abstr. 1986, 107, 96347v; Patschorke, J., Patentschrift (Switz.) CH 657,862, 1986; Chem. Abstr. 1986, 106, 70316p; Dahbi, T.P., Shah, V.H., Parikh, A.R., (1992) Indian J. Heterocycl. Chem., 2 (2), p. 137
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  • We thank one of the referees for this comment; Viruela-Martin, P., Viruela-Martin, R., Tomas, F., Nudelman, N.S., (1994) J. Am. Chem. Soc., 116, p. 10110
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Citas:

---------- APA ----------
Nudelman, N.S., Schulz, H., Liñares, G.G., Bonatti, A. & Boche, G. (1998) . Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H). Organometallics, 17(2), 146-150.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v17_n2_p146_Nudelman [ ]
---------- CHICAGO ----------
Nudelman, N.S., Schulz, H., Liñares, G.G., Bonatti, A., Boche, G. "Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H)" . Organometallics 17, no. 2 (1998) : 146-150.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v17_n2_p146_Nudelman [ ]
---------- MLA ----------
Nudelman, N.S., Schulz, H., Liñares, G.G., Bonatti, A., Boche, G. "Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H)" . Organometallics, vol. 17, no. 2, 1998, pp. 146-150.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v17_n2_p146_Nudelman [ ]
---------- VANCOUVER ----------
Nudelman, N.S., Schulz, H., Liñares, G.G., Bonatti, A., Boche, G. Further insights into the chemistry of acyllithium compounds R2NC(O)Li: Characterization of an amide (R2NLi) adduct (R2NCHNR2(OLi)) to a formamide (R2NC(O)H). Organometallics. 1998;17(2):146-150.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02767333_v17_n2_p146_Nudelman [ ]