Artículo
Doctorovich, F.; Trápani, C. "The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines" (1999) Tetrahedron Letters. 40(25):4635-4638
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Abstract:
Pentacyanonitrosylferrate(II), 1, reacts with n-butylamine to produce di-n-butylamine in high yields (81-95%). The absence of rearranged products indicates that the initially produced diazonium ion is stabilized by coordination to the metal. Benzylamine and 1,4-diaminobutane react with 1 to produce dibenzylamine and piperidine, respectively.
Registro:
| Documento: | Artículo |
| Título: | The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines |
| Autor: | Doctorovich, F.; Trápani, C. |
| Filiación: | Depto. de Quím. Inorganica, Analitica y Quim. Fis./INQUIMAE, Fac. de Ciensias Exactasy Naturales, Pabellón II, piso 3, 1428 Buenos Aires, Argentina |
| Palabras clave: | Amine; Complex; Diazotization; Iron; Nitroprusside; Pentacyanonitrosylferrate; aliphatic compound; amine; benzylamine; butylamine; coordination compound; diazonium compound; dibenzylamine; dibutylamine; iron derivative; metal; pentacyanonitrosylferrate(ii); piperidine; putrescine; unclassified drug; article; chemical reaction; reaction analysis; synthesis |
| Año: | 1999 |
| Volumen: | 40 |
| Número: | 25 |
| Página de inicio: | 4635 |
| Página de fin: | 4638 |
| DOI: | http://dx.doi.org/10.1016/S0040-4039(99)00810-2 |
| Título revista: | Tetrahedron Letters |
| Título revista abreviado: | Tetrahedron Lett. |
| ISSN: | 00404039 |
| CODEN: | TELEA |
| CAS: | benzylamine, 100-46-9, 2182-52-7, 3287-99-8; butylamine, 109-73-9; dibenzylamine, 103-49-1, 20455-68-9; piperidine, 110-89-4, 6091-44-7; putrescine, 110-60-1, 333-93-7 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v40_n25_p4635_Doctorovich |
Referencias:
- Nathan, C., Xie, Q.W., (1994) Cell, 78, p. 915
- Fricker, S.P., (1995) Platinum Metals Rev., 39, p. 150
- Dózsa, L., Kormos, V., Beck, M.T., (1984) Inorg. Chimica Acta, 82, p. 69
- Doctorovich, F., Estrin, D., Turjanski, A., in preparation; Bowden, W.L., Little, W.F., Meyer, T.J., (1977) J. Am. Chem. Soc., 99, p. 4340
- Butler, A.R., Glidewell, C., Reglinski, J., Waddon, A., (1984) J. Chem. Res., Synop., 9, p. 279
- Casado, J., Mosquera, M., Rodríguez Prieto, M.F., Vázquez Tato, J., (1985) Ber. Bunsenges. Phys. Chem., 89, p. 735
- Beck, M.T., Kathó, A., Dózsa, L., (1981) Inorg. Chimica Acta, 55, pp. L55
- Streitwieser A., Jr., Schaeffer, W.D., (1957) J. Am. Chem. Soc., 79, p. 2888
- Adcock, P.A., Keene, F.R., Smythe, R.S., Snow, M.R., (1984) Inorg. Chem., 23, p. 2336
- Bowden, W.L., Bonnar, P., Brown, D.B., Geiger, W.E., (1976) Inorg. Chem., 16, p. 41
- Keene, F.R., Salmon, D.J., Meyer, T.J., (1976) J. Am. Chem. Soc., 98, p. 1884
- Diamond, S.E., Tom, G.M., Taube, H.J., (1975) J. Am. Chem. Soc., 97, p. 2661
- Adcock, P.A., Keene, F.R., (1981) J. Am. Chem. Soc., 103, p. 6494
- Olabe, J.A., Zerga, H.O., (1983) Inorg. Chem., 22, p. 4156
- March, J., (1992) Advanced Organic Chemistry, , John Wiley: New York
Citas:
---------- APA ----------
Doctorovich, F. & Trápani, C. (1999) . The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines. Tetrahedron Letters, 40(25), 4635-4638.http://dx.doi.org/10.1016/S0040-4039(99)00810-2
---------- CHICAGO ----------
Doctorovich, F., Trápani, C. "The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines" . Tetrahedron Letters 40, no. 25 (1999) : 4635-4638.http://dx.doi.org/10.1016/S0040-4039(99)00810-2
---------- MLA ----------
Doctorovich, F., Trápani, C. "The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines" . Tetrahedron Letters, vol. 40, no. 25, 1999, pp. 4635-4638.http://dx.doi.org/10.1016/S0040-4039(99)00810-2
---------- VANCOUVER ----------
Doctorovich, F., Trápani, C. The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines. Tetrahedron Lett. 1999;40(25):4635-4638.http://dx.doi.org/10.1016/S0040-4039(99)00810-2
