A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides

N-nitrosoalkylamines were efficiently synthesized from the reaction of lithium amides with NO at atmospheric pressure using dialkylamines as starting materials. With asymmetric amines stereoselectivity is observed giving rise to different amounts of E and Z isomers.

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Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Bonatti, A.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2000
Acceso en línea:Registro en Scopus
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Registro en la Biblioteca Digital
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024 7 |2 cas  |a amide, 17655-31-1; lithium, 7439-93-2; nitric oxide, 10102-43-9; nitrosamine, 35576-91-1 
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100 1 |a Nudelman, N.S. 
245 1 2 |a A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides 
260 |c 2000 
270 1 0 |m Nudelman, N.S.; Pab. II, P. 3, Cdad Universitaria 1428 Buenos Aires, Argentina; email: nudelman@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
504 |a Gdaniec, M., Milewska, M.J., Polonski, T., (1995) J. Org. Chem., 60, pp. 7411-7418 
504 |a Fishbein, J.C., Chahoua, L., Mesic, M., Revis, C.L., Vigroux, A., (1997) J. Org. Chem., 62, pp. 2500-2504 
504 |a Fishbein, J.C., Chahoua, L., Mesic, M., (1996) J. Org. Chem., 61, p. 1512 
504 |a Fishbein, J.C., Revis, C.L., Rajamaki, M., (1995) J. Org. Chem., 60, p. 7733 
504 |a Fishbein, J.C., Rajamaki, M., Vigroux, A., Chahoua, L., (1995) J. Org. Chem., 60, p. 2324 
504 |a Feelisch, M., Stamler, J.S., (1996) Methods in Nitric Oxide Research, , Feelisch M. and Stamler J. S., eds; Wiley, Chichester; ch. 7 
504 |a (1998) Dictionary of Organic Compounds on CD-ROM, version 6:1, , Chapman and Hall, London 
504 |a Montague, P.R., Gancayco, C.D., Winn, M.J., Marchase, R.B., Friedlander, M.J., (1994) Science, 263, p. 973 
504 |a Brown, (1994) The Organic Chemistry of Aliphatic Nitrogen Compounds, , ch. 12, Oxford 
504 |a Garcia Rio, L., Leis, J.L., Iglesias, E., (1997) J. Org. Chem., 62, pp. 4701-4711 
504 |a Goldstein, S., Czapski, G., (1996) J. Am. Chem. Soc., 118, pp. 3419-3425 
504 |a Mehler, A.H., Nitric oxide from arginine: A biological surprise (1996), The chemistry of amino, nitroso, nitro and related groups Part 2; Patai S., Ed.; Wiley, Chichester; Itoh, T., Nagata, K., Matsuya, Y., Miyazaki, M., Ohsawa, A., (1997) Tetrahedron Lett., 38, pp. 5017-5020 
504 |a Mukaiyama, T., Hata, E., Yamada, T., (1995) Chem. Lett., p. 505 
504 |a Nagano, T., Takizawa, H., Hirobe, M., (1995) Tetrahedron Lett., 36, p. 8239 
504 |a Collet, H., Bied, C., Mion, L., Taillades, J., Commeyras, A., (1996) Tetrahedron Lett., 37, p. 9043 
504 |a Abraham, M.H., Bullock, J.I., Garland, J.H.N., Golder, A.J., Harden, G.J., Larkworthy, L.F., Povey, D.C., Smith, G.W., (1987) Polyhedron, 6, p. 1375 
504 |a Nudelman, N.S., Doctorovich, F., (1994) Tetrahedron, 50, p. 4651 
504 |a Nudelman, N.S., Carbonylation of main-group organometallic compounds (1989), The Chemistry of Double Bonded Functional Groups; Patai S., Ed.; Wiley, Chichester; Seyferth, D., Hui, R.C., Wang, W.L., (1993) J. Org. Chem., 58, p. 5843 
504 |a Nudelman, N.S., Schulz, H., Garcia Linares, G., Bonatti, A., Boche, G., (1998) Organometallics, 17, pp. 146-150 
504 |a Nudelman, N.S., Garcia Linares, G., (2000) J. Org. Chem., 65, p. 1629 
504 |a Adler, M., Marsch, M., Nudelman, N.S., Boche, G., (1999) Angew. Chem. Int. Ed. Engl., 38, p. 1261 
504 |a note; Cerioni, G., Giumanini, A.G., Verardo, G., Dahn, H., (1994) Magn. Reson. Chem., 32, p. 46 
504 |a Milewska, M.J., Polonski, T., (1994) Magn. Reson. Chem., 32, p. 631 
504 |a Nudelman, N.S., Schulz, H., (2000) J. Chem. Soc. Perkin Trans. 2, p. 1619 
504 |a Taha, A.N., Neugebauer Crawford, S.M., True, N.S., (1998) J. AM. Chem. Soc., 120, p. 1934 
520 3 |a N-nitrosoalkylamines were efficiently synthesized from the reaction of lithium amides with NO at atmospheric pressure using dialkylamines as starting materials. With asymmetric amines stereoselectivity is observed giving rise to different amounts of E and Z isomers.  |l eng 
593 |a Pab. II, P. 3, Cdad Universitaria 1428 Buenos Aires, Argentina 
690 1 0 |a ALKYL NITROSAMINES 
690 1 0 |a LITHIUM AMIDES 
690 1 0 |a NITROSAMINES 
690 1 0 |a NITROSATION 
690 1 0 |a NO REACTIVITY 
690 1 0 |a AMIDE 
690 1 0 |a LITHIUM 
690 1 0 |a NITRIC OXIDE 
690 1 0 |a NITROSAMINE 
690 1 0 |a ARTICLE 
690 1 0 |a ATMOSPHERIC PRESSURE 
690 1 0 |a CHEMICAL REACTION 
690 1 0 |a METHODOLOGY 
690 1 0 |a NITROSATION 
690 1 0 |a STEREOCHEMISTRY 
690 1 0 |a SYNTHESIS 
700 1 |a Bonatti, A.E. 
773 0 |d 2000  |h pp. 1825-1827  |k n. 12  |p Synlett  |x 09365214  |w (AR-BaUEN)CENRE-77  |t Synlett 
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