New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2)

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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 carbam...

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Autor principal: Nudelman, N.S
Otros Autores: García Liñares, G.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2000
Acceso en línea:Registro en Scopus
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100 1 |a Nudelman, N.S. 
245 1 0 |a New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2) 
260 |c 2000 
270 1 0 |m Nudelman, N.S.; Departamento de Quimica Organica, Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Ball, S.C., Cragg-Hine, I., Davidson, M.G., Davies, R.P., Raithby, P.R., Snaith, R., (1996) J. Chem. Soc., Chem. Commun., p. 1581 
504 |a Müller, A., Marsch, M., Harms, K., Lohrenz, J.C.W., Boche, G., (1996) Angew. Chem., Int. Ed. Engl., 35, p. 1518 
504 |a Stiasny, H.C., Böhm, V.P.W., Hoffman, R.W., (1997) Chem. Ver., 130, p. 341 
504 |a Nudelman, N.S., Schulz, H., García Liñares, G., Bonatti, A., Boche, G., (1998) Organometallics, 17, p. 146 
504 |a Seyferth, D., Hui, R.C., Wang, W.L., (1993) J. Org. Chem., 58, p. 5843. , and references cited therein 
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 Davidson, M.G., Davies, R.P., Raithby, P.R., Snaith, R., (1996) J. Chem. Soc., Chem. Commun., p. 1695 
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, p. 917 
504 |a Perez, D.G., Nudelman, N.S., (1988) J. Org. Chem., 53, p. 408 
504 |a Abu-Hasanayn, F., Streitwieser, A., (1998) J. Org. Chem., 63, p. 2954 
504 |a Leung, S.S.-W., Streitwieser, A., (1998) J. Am. Chem. Soc., 720, p. 10557 
504 |a Thompson, A., Corley, E.G., Huntington, M.F., Grabowski, E.J.J., Remenar, J.F., Collum, D.B., (1998) J. Am. Chem. Soc., 120, p. 2028 
504 |a Henderson, K.W., Dorigo, A.E., Williard, P.G., Bernstein, P.R., (1996) Angew. Chem., Int. Ed. Engl., 35, p. 1322 
504 |a Ball, S.C., Cragg-Hine, I., Davidson, M.G., Davies, R.P., Edwards, A.J., Lopez-Solera, I., Raithby, P.R., Snaith, R., (1995) Angew. Chem., Int. Ed. Engl., 34, p. 1002 
504 |a Weiss, E., (1993) Angew. Chem., Int. Ed. Engl., 32, p. 1501 
504 |a Mulvey, R., (1991) Chem. Soc. Rev., 20, p. 167 
504 |a Waldmüller, D., Kotsatos, B.J., Nichols, M.A., Williard, P.G., (1997) J. Am. Chem. Soc., 119, p. 5479 
504 |a Abbotto, A., Streitwieser, A., Schleyer, P.V.R., (1997) J. Am. Chem. Soc., 119, p. 11255 
504 |a Bauer, W., (1996) J. Am. Chem. Soc., 118, p. 5450 
504 |a Williard, P.G., Sun, C., (1997) J. Am. Chem. Soc., 119, p. 11693 
504 |a Boche, G., Langlotz, I., Marsch, M., Harms, K., Nudelman, N.S., (1992) Angew. Chem., Int. Ed. Engl., 104, p. 774 
504 |a Van Vliet, G.L.J., De Kanter, F.J.J., Schakel, M., Klumpp, G.W., Spek, A.L., Lutz, M., (1999) Chem. Eur. J., 5, p. 1091 
504 |a Clegg, W., Henderson, K.W., Horsburgh, L., Mackenzie, F.M., Mulvey, R.E., (1998) Chem.-Eur. J., 4, p. 53 
504 |a Hilmersson, G., Arvidsson, P.I., Davidsson, Ö., Hakansson, M., (1998) J. Am. Chem. Soc., 120, p. 8143 
504 |a Bauer, W., (1996) Magn. Reson. Chem., 34, p. 532 
504 |a Hüls, D., Günther, H., Van Koten, G., Wijkens, P., Jastrzebski, J.T.B.H., (1997) Angew. Chem., Int. Ed. Engl., 36, p. 2629 
504 |a Khanjin, N.A., Menger, F.M., (1997) J. Org. Chem., 62, p. 8923 
504 |a Aubrecht, K.B., Collum, D.B., (1996) J. Org. Chem., 61, p. 8674 
504 |a Remenar, J.F., Lucht, B.L., Collum, D.B., (1997) J. Am. Chem. Soc., 119, p. 5567 
504 |a Corruble, A., Valnot, J.-Y., Maddaluno, J., Prigent, Y., Davoust, D., Duhamel, P., (1997) J. Am. Chem. Soc., 119, p. 10042 
504 |a Nudelman, N.S., Lewkowicz, E.S., Furlong, J.P.J., (1993) J. Org. Chem., 58, p. 1847 
504 |a Nudelman, N.S., (1998) Pure Appl. Chem., 70, p. 1939 
504 |a Dahbi, T.P., Shah, V.H., Parikh, A.R., (1992) Indian J. Heterocycl. Chem., 2 (2), p. 137 
504 |a Nudelman, N.S., García Liñares, G., Schulz, H., (1995) Main Group Metal Chem., 18, p. 147 
504 |a McCusker, J.E., Abboud, K.A., McElwee-White, L., (1997) Organometallics, 16, p. 3863 
504 |a Rülke, R.E., Dolis, J.G.P., Grost, A.M., Elsevier, C.J., Van Leeuween, P.W.N.M., Vrieze, K., Goubitz, K., Schenk, H., (1996) J. Organomet. Chem., 511, p. 47 
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. Arg., p. 619 
504 |a Chaplinski, V., De Meijere, A., (1996) Angew. Chem., Int. Ed. Engl., 35, p. 413 
504 |a Adler, M., Marsch, M., Nudelman, N.S., Boche, G., (1999) Angew. Chem., Int. Ed. Engl., 38, p. 1261 
504 |a Smith, R.M., Hansen, D.E., (1998) J. Am. Chem. Soc., 120, p. 8910 
504 |a Venturini, A., López-Ortiz, F., Alvarez, J.M., González, J., (1998) J. Am. Chem. Soc., 120, p. 1110 
504 |a Adalsteinsson, H., Bruice, T.C., (1998) J. Am. Chem. Soc., 120, p. 3440 
504 |a Bürgi, H.B., Dunitz, J.D., Lehn, J.M., Wipff, G., (1974) Tetrahedron, 30, p. 1563 
504 |a Bürgi, H.B., Dunitz, J.D., Lehn, J.M., Wipff, G., (1974) J. Am. Chem. Soc., 96, p. 1956 
504 |a Furlong, J.J.P., Lewkowicz, E.S., Nudelman, N.S., (1990) J. Chem. Soc., Perkin Trans. 2, p. 1461 
504 |a Rautenstrauch, V., Joyeaux, M., (1979) Angew. Chem., Int. Ed. Engl., 18, p. 83 
504 |a Lauvergnat, D., Hiberty, P.C., (1997) J. Am. Chem. Soc., 119, p. 9478 
504 |a Wiberg, K.B., Rablen, P.R., (1995) J. Am. Chem. Soc., 117, p. 2201 
504 |a Ball, S.C., Cragg-Hine, I., Davidson, M.G., Davies, R.P., Edwards, A.J., Lopez-Solera, I., Raithby, P.R., Snaith, R., (1995) Angew. Chem., Int. Ed. Engl., 34, p. 921 
504 |a Ball, S.C., Cobb, J., Davies, R.P., Raithby, P.R., Shields, G.P., Snaith, R., (1997) J. Organomet. Chem., 534, p. 241 
504 |a Viruela-Martin, P., Viruela-Martin, R., Tomas, F., Nudelman, N.S., (1994) J. Am. Chem. Soc., 116, p. 10110 
504 |a Arduengo A.J. III, Harlow, R.L., Kline, M., (1991) J. Am. Chem. Soc., 113, p. 361 
504 |a Boche, G., Marsch, M., Müller, A., Harms, K., (1993) Angew. Chem., Int. Ed. Engl., 32, p. 1032 
504 |a Zuev, P.S., Sheridan, R.S., (1994) J. Am. Chem. Soc., 116, p. 4123 
504 |a Arduengo A.J. III, Dias, H.V.R., Harlow, R.L., Kline, M., (1992) J. Am. Chem. Soc., 114, p. 5530 
504 |a Arduengo A.J. III, Dias, H.V.R., Calabrese, J.C., Davidson, F., (1992) J. Am. Chem. Soc., 114, p. 9724 
504 |a Shriver, D.F., Drezdzon, M.A., (1986) The Manipulation of Air-Sensitive Compounds, 2nd Ed., , Wiley: New York 
504 |a Nudelman, N.S., Pérez, D., Galloy, J., Watson, W., (1983) Acta Crystallogr., Sect. C: Cryst. Struct. Commun., C39, p. 393 
520 3 |a 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.  |l eng 
593 |a Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, P. 3, 1428 Buenos Aires, Argentina 
690 1 0 |a 1 FORMYLPIPERIDINE 
690 1 0 |a 4 FORMYLMORPHOLINE 
690 1 0 |a FORMAMIDE DERIVATIVE 
690 1 0 |a GLYOXYLAMIDE 
690 1 0 |a LITHIUM DICYCLOHEXYLAMIDE 
690 1 0 |a N,N DIBUTYLFORMAMIDE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ARTICLE 
690 1 0 |a CARBON NUCLEAR MAGNETIC RESONANCE 
690 1 0 |a CHEMICAL BINDING 
690 1 0 |a CHEMICAL REACTION KINETICS 
690 1 0 |a ORGANIC CHEMISTRY 
690 1 0 |a QUANTITATIVE ASSAY 
690 1 0 |a REACTION ANALYSIS 
690 1 0 |a STRUCTURE ANALYSIS 
700 1 |a García Liñares, G.E. 
773 0 |d 2000  |g v. 65  |h pp. 1629-1635  |k n. 6  |p J. Org. Chem.  |x 00223263  |w (AR-BaUEN)CENRE-337  |t Journal of Organic Chemistry 
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856 4 0 |u https://doi.org/10.1021/jo9908445  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00223263_v65_n6_p1629_Nudelman  |y Handle 
856 4 0 |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v65_n6_p1629_Nudelman  |y Registro en la Biblioteca Digital 
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