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)

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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-for...

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Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Schulz, H., Liñares, G.G, Bonatti, A., Boche, G.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1998
Acceso en línea:Registro en Scopus
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Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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100 1 |a Nudelman, N.S. 
245 1 0 |a 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) 
260 |c 1998 
270 1 0 |m Nudelman, N.S.; Depto. de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Univ. de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Gregory, K., Schleyer, P.V.R., Snaith, R., (1991) Adv. Inorg. Chem., 37, p. 47 
504 |a Mulvey, R.E., (1991) Chem. Soc. Rev., 20, p. 167 
504 |a Nudelman, N.S., Carbonylation of Main-Group Organometal Compounds (1989) The Chemistry of Double Bonded Functional Groups, , Patai, S., Ed.; Wiley, Chichester 
504 |a Collum, D.B., (1993) Acc. Chem. Res., 26, p. 227 
504 |a Nichols, M.A., Waldmüller, D., Williard, P.G., (1994) J. Am. Chem. Soc., 116, p. 1153 
504 |a Nudelman, N.S., Lewkowicz, E.S., Furlong, J.J.P., (1993) J. Org. Chem., 58, p. 1847 
504 |a Lucht, B.L., Collum, D.B., (1995) J. Am. Chem. Soc., 117, p. 9863 
504 |a Lucht, B.L., Collum, D.B., (1994) J. Am. Chem. Soc., 116, p. 6009 
504 |a Lucht, B.L., Collum, D.B., (1996) J. Am. Chem. Soc., 118, p. 2217 
504 |a Nudelman, N.S., Lewkowicz, E.S., Perez, D.G., (1990) Synthesis, 10, p. 917 
504 |a Vedejs, E., Lee, N., (1995) J. Am. Chem. Soc., 117, p. 891. , and previous references 
504 |a Boche, G., Langlotz, I., Marsch, M., Harms, K., Nudelman, N.S., (1992) Angew. Chem., Int. Ed. Engl., 104, p. 774 
504 |a Pérez, D.G., Nudelman, N.S., (1988) J. Org. Chem., 53, p. 408 
504 |a Pérez, D.G., Nudelman, N.S., (1983) J. Org. Chem., 48, p. 133 
504 |a Bitsi, G., Jenner, G., (1987) J. Organomet. Chem., 330 (3), p. 429 
504 |a Nudelman, N.S., García Liñares, G., Schulz, H., (1995) Main Group Met. Chem., 78, p. 147 
504 |a Nudelman, N.S., Doctorovich, F., García Liñares, G., Schulz, H., (1996) Gazz. Chim. Ital., 126, p. 19 
504 |a Nudelman, N.S., García Liñares, G., (1996) An. Asoc. Quim. Argent., p. 619 
504 |a 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 
504 |a Waver, I., Osek, J., (1985) J. Chem. Soc., Perkin Trans. 2, p. 1669 
504 |a Furlong, J.J.P., Lewkowicz, E.S., Nudelman, N.S., (1990) J. Chem. Soc., Perkin Trans.2, p. 1461 
504 |a Fraenkel, G., Subramanian, S., Chow, A., (1995) J. Am. Chem. Soc., 117, p. 6300 
504 |a 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 
504 |a Pretsch, E., ChemWindow 3, Version 3.0.0.C13, , Department of Organic Chemistry, ETH, Zurich, Switzerland 
504 |a Majewski, M., Gleave, D.M., (1994) J. Organomet. Chem., 470, p. 1 
504 |a Shriver, D.F., Drezdzon, M.A., (1986) The Manipulation of Air-Sensitive Compounds, 2nd Ed., , Wiley: New York 
520 3 |a 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.  |l eng 
593 |a Depto. de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Univ. de Buenos Aires, Pab. II, P. 3, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Fachbereich Chemie, Philipps-Universitat Marburg, Marburg, Germany 
700 1 |a Schulz, H. 
700 1 |a Liñares, G.G. 
700 1 |a Bonatti, A. 
700 1 |a Boche, G. 
773 0 |d 1998  |g v. 17  |h pp. 146-150  |k n. 2  |p Organometallics  |x 02767333  |w (AR-BaUEN)CENRE-2351  |t Organometallics 
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999 |c 63951 

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