Abstract:
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.
Registro:
Documento: |
Artículo
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Título: | A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides |
Autor: | Nudelman, N.S.; Bonatti, A.E. |
Filiación: | Pab. II, P. 3, Cdad Universitaria 1428 Buenos Aires, Argentina
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Palabras clave: | Alkyl nitrosamines; Lithium amides; Nitrosamines; Nitrosation; NO reactivity; amide; lithium; nitric oxide; nitrosamine; article; atmospheric pressure; chemical reaction; methodology; nitrosation; stereochemistry; synthesis |
Año: | 2000
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Número: | 12
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Página de inicio: | 1825
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Página de fin: | 1827
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Título revista: | Synlett
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Título revista abreviado: | Synlett
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ISSN: | 09365214
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CODEN: | SYNLE
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CAS: | amide, 17655-31-1; lithium, 7439-93-2; nitric oxide, 10102-43-9; nitrosamine, 35576-91-1
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09365214_v_n12_p1825_Nudelman |
Referencias:
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- Fishbein, J.C., Chahoua, L., Mesic, M., (1996) J. Org. Chem., 61, p. 1512
- Fishbein, J.C., Revis, C.L., Rajamaki, M., (1995) J. Org. Chem., 60, p. 7733
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- Feelisch, M., Stamler, J.S., (1996) Methods in Nitric Oxide Research, , Feelisch M. and Stamler J. S., eds; Wiley, Chichester; ch. 7
- (1998) Dictionary of Organic Compounds on CD-ROM, version 6:1, , Chapman and Hall, London
- Montague, P.R., Gancayco, C.D., Winn, M.J., Marchase, R.B., Friedlander, M.J., (1994) Science, 263, p. 973
- Brown, (1994) The Organic Chemistry of Aliphatic Nitrogen Compounds, , ch. 12, Oxford
- Garcia Rio, L., Leis, J.L., Iglesias, E., (1997) J. Org. Chem., 62, pp. 4701-4711
- Goldstein, S., Czapski, G., (1996) J. Am. Chem. Soc., 118, pp. 3419-3425
- 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
- Mukaiyama, T., Hata, E., Yamada, T., (1995) Chem. Lett., p. 505
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- Collet, H., Bied, C., Mion, L., Taillades, J., Commeyras, A., (1996) Tetrahedron Lett., 37, p. 9043
- 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
- Nudelman, N.S., Doctorovich, F., (1994) Tetrahedron, 50, p. 4651
- 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
- Nudelman, N.S., Schulz, H., Garcia Linares, G., Bonatti, A., Boche, G., (1998) Organometallics, 17, pp. 146-150
- Nudelman, N.S., Garcia Linares, G., (2000) J. Org. Chem., 65, p. 1629
- Adler, M., Marsch, M., Nudelman, N.S., Boche, G., (1999) Angew. Chem. Int. Ed. Engl., 38, p. 1261
- note; Cerioni, G., Giumanini, A.G., Verardo, G., Dahn, H., (1994) Magn. Reson. Chem., 32, p. 46
- Milewska, M.J., Polonski, T., (1994) Magn. Reson. Chem., 32, p. 631
- Nudelman, N.S., Schulz, H., (2000) J. Chem. Soc. Perkin Trans. 2, p. 1619
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Citas:
---------- APA ----------
Nudelman, N.S. & Bonatti, A.E.
(2000)
. A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides. Synlett(12), 1825-1827.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09365214_v_n12_p1825_Nudelman [ ]
---------- CHICAGO ----------
Nudelman, N.S., Bonatti, A.E.
"A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides"
. Synlett, no. 12
(2000) : 1825-1827.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09365214_v_n12_p1825_Nudelman [ ]
---------- MLA ----------
Nudelman, N.S., Bonatti, A.E.
"A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides"
. Synlett, no. 12, 2000, pp. 1825-1827.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09365214_v_n12_p1825_Nudelman [ ]
---------- VANCOUVER ----------
Nudelman, N.S., Bonatti, A.E. A highly convenient new methodology for the synthesis of N-nitrosamines from lithium amides. Synlett. 2000(12):1825-1827.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09365214_v_n12_p1825_Nudelman [ ]