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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Detalles Bibliográficos
Autor principal: Nudelman, N.S
Otros Autores: Socolovsky, S.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1980
Acceso en línea:Registro en Scopus
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100 1 |a Nudelman, N.S. 
245 1 0 |a Unusual dealkylations and rearrangements in aromatic nucleophilic substitution 
260 |c 1980 
270 1 0 |m Nudelman, N.S.; Depto de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a 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 
504 |a Nudelman, (1978) Anales Asoc. Quím. Arg., 66, p. 89 
504 |a Kolthoff, Guss, (1938) J. Am. Chem. Soc., 60, p. 2516 
504 |a Bunnett, Nudelman, (1969) J. Org. Chem., 34, p. 2043 
504 |a Ainsworth, Easton, Thermal Elimination Reaction of Aliphatic Amine Salts (1962) The Journal of Organic Chemistry, 24, p. 4118 
504 |a Schölkopf, Recent Results in Carbanion Chemistry (1970) Angewandte Chemie International Edition in English, 9, p. 763. , Int. Ed. Engl 
504 |a Nudelman, Garrido, (1976) J. Chem. Soc., p. 1256. , Perkin Trans. II 
504 |a 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 
504 |a Bunnett, Kato, Nudelman, (1969) J. Org. Chem., 34, p. 785 
504 |a Nudelman, Brieux, (1970) Anales Asoc. Quím. Arg., 58, p. 217 
504 |a Bernasconi, (1973) MTP Int. Rev. Sci., Org. Chem., 3, p. 33. , Ser. One 
520 3 |a 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.  |l eng 
536 |a Detalles de la financiación: CientSficaa y TE?cnicas (bgentina) ACKNOWLEDCMF and from the Organization of the AmericanS tates is grate-ESN: Financial support from the Cbnsejo National de Investigaciones fully acknowledged. 
593 |a Depto de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina 
700 1 |a Socolovsky, S.E. 
773 0 |d 1980  |g v. 21  |h pp. 3331-3334  |k n. 35  |p Tetrahedron Lett.  |x 00404039  |w (AR-BaUEN)CENRE-415  |t Tetrahedron Letters 
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856 4 0 |u https://hdl.handle.net/20.500.12110/paper_00404039_v21_n35_p3331_Nudelman  |y Handle 
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