Artículo
Nudelman, N.S.; Socolovsky, S.E. "Unusual dealkylations and rearrangements in aromatic nucleophilic substitution" (1980) Tetrahedron Letters. 21(35):3331-3334
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Abstract:
The reaction of 2,4-dinitrohalobenzenes with di-isopropylamine produces mainly N-(2,4-dinitrophenyl)-isopropylamine and N-(2,4-dinitrophenyl)-n-propylamine instead of the expected straightforward substitution product. Dealkylations are also observed in the reactions with isopropylcyclohexylamine and dicyclohexylamine. A carbanionic mechanism is proposed. © 1980.
Registro:
| Documento: | Artículo |
| Título: | Unusual dealkylations and rearrangements in aromatic nucleophilic substitution |
| Autor: | Nudelman, N.S.; Socolovsky, S.E. |
| Filiación: | Depto de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina |
| Año: | 1980 |
| Volumen: | 21 |
| Número: | 35 |
| Página de inicio: | 3331 |
| Página de fin: | 3334 |
| DOI: | http://dx.doi.org/10.1016/S0040-4039(00)78681-3 |
| Título revista: | Tetrahedron Letters |
| Título revista abreviado: | Tetrahedron Lett. |
| ISSN: | 00404039 |
| CODEN: | TELEA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v21_n35_p3331_Nudelman |
Referencias:
- Nudelman, ortho Effects on Nucleophilic Aromatic Substitution. The Reactions of 6-R-2-Nitrochlorobenzenes with Piperidine in Benzene (1965) The Journal of Organic Chemistry, 30, p. 3365
- Nudelman, (1978) Anales Asoc. Quím. Arg., 66, p. 89
- Kolthoff, Guss, (1938) J. Am. Chem. Soc., 60, p. 2516
- Bunnett, Nudelman, (1969) J. Org. Chem., 34, p. 2043
- Ainsworth, Easton, Thermal Elimination Reaction of Aliphatic Amine Salts (1962) The Journal of Organic Chemistry, 24, p. 4118
- Schölkopf, Recent Results in Carbanion Chemistry (1970) Angewandte Chemie International Edition in English, 9, p. 763. , Int. Ed. Engl
- Nudelman, Garrido, (1976) J. Chem. Soc., p. 1256. , Perkin Trans. II
- Benzene was kept over sodium strings several days and twice distilled over sodium (water content≤0.02% by Karl-Fisher method); Nudelman, Brieux, (1970) Anales Asoc. Quím. Arg., 58, p. 217
- Bunnett, Kato, Nudelman, (1969) J. Org. Chem., 34, p. 785
- Nudelman, Brieux, (1970) Anales Asoc. Quím. Arg., 58, p. 217
- Bernasconi, (1973) MTP Int. Rev. Sci., Org. Chem., 3, p. 33. , Ser. One
Citas:
---------- APA ----------
Nudelman, N.S. & Socolovsky, S.E. (1980) . Unusual dealkylations and rearrangements in aromatic nucleophilic substitution. Tetrahedron Letters, 21(35), 3331-3334.http://dx.doi.org/10.1016/S0040-4039(00)78681-3
---------- CHICAGO ----------
Nudelman, N.S., Socolovsky, S.E. "Unusual dealkylations and rearrangements in aromatic nucleophilic substitution" . Tetrahedron Letters 21, no. 35 (1980) : 3331-3334.http://dx.doi.org/10.1016/S0040-4039(00)78681-3
---------- MLA ----------
Nudelman, N.S., Socolovsky, S.E. "Unusual dealkylations and rearrangements in aromatic nucleophilic substitution" . Tetrahedron Letters, vol. 21, no. 35, 1980, pp. 3331-3334.http://dx.doi.org/10.1016/S0040-4039(00)78681-3
---------- VANCOUVER ----------
Nudelman, N.S., Socolovsky, S.E. Unusual dealkylations and rearrangements in aromatic nucleophilic substitution. Tetrahedron Lett. 1980;21(35):3331-3334.http://dx.doi.org/10.1016/S0040-4039(00)78681-3
