Unusual dealkylations and rearrangements in aromatic nucleophilic substitution
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...
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| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
1980
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| Sumario: | 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. |
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| Bibliografía: | 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 |
| ISSN: | 00404039 |
| DOI: | 10.1016/S0040-4039(00)78681-3 |