Structural and spectroscopic investigation of 1-amino-2,4-dinitrobenzenes

Remedi, M. Virginia; Bujn, Elba I.; Baggio, Ricardo; Garland, M. T.

doi:10.1002/(sici)1099-1395(199812)11:12<895::aid-poc79>3.0.co;2-5

Cited by 5 publications

(1 citation statement)

References 21 publications

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“…As reações mostraram-se extremamente reprodutíveis, de fácil execução em variações de escala de 1 a 10 g, por agitação da mistura reacional por cerca de 1 h em DMF. 9,10 Um ligeiro aquecimento foi necessário para o deslocamento com imidazol (Esquema 2). Os produtos brutos de isolamento, após secagem, foram caracterizados por infravermelho (IV), espectrometria de massas (EM) e ressonância magnética nuclear (RMN).…”

Section: Esquemaunclassified

Preparação de N-alquil derivados do 1-bromo-2,4-dinitrobenzeno e do 1-cloro-2-nitrobenzeno: Uma alternativa às aulas práticas de substituição nucleofílica aromática

Dias¹,

Pereira²,

Soares³

2008

Quím. Nova

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PreParação de N-alquil derivados do 1-bromo-2,4-dinitrobenzeno e do 1-cloro-2-nitrobenzeno. uma alternativa às aulas Práticas de substituição nucleofílica aromática ayres Guimarães dias*, felipe martins alves Pereira e renato de oliveira soares Departamento de Química Orgânica, Instituto de Química, Universidade do Estado do Rio de Janeiro, R. São Francisco Xavier, 524, Pavilhão Haroldo Lisboa, 20559-900 Rio de Janeiro -RJ, BrasilRecebido em 20/6/07; aceito em 29/2/08; publicado na web em 1/10/08 PREPARATION OF N-ALKYL DERIVATIVES OF 1-BROMO-2,4-DINITROBENZENE AND 1-CHLORO-2-NITROBENZENE. AN ALTERNATIVE TO NUCLEOPHILIC AROMATIC SUBSTITUTION PRACTICES. Preparation of the title compounds are described as an alternative nucleophilic aromatic substitution for practices in the graduate laboratory. The low toxicity and disponibility of the reagents make a suitable procedure approach to experiments regarding this aromatic reaction.

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Section: Esquemaunclassified

Preparação de N-alquil derivados do 1-bromo-2,4-dinitrobenzeno e do 1-cloro-2-nitrobenzeno: Uma alternativa às aulas práticas de substituição nucleofílica aromática

Dias¹,

Pereira²,

Soares³

2008

Quím. Nova

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Medium Effect on the Reaction of N‐Butyl‐2,4,6‐trinitroaniline with NaOH

2007

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The kinetics of the reaction of N‐butyl‐2,4,6‐trinitroaniline (3) with NaOH have been studied in 10 and 60 % 1,4‐dioxane/H2O at 25 °C. In both cases, several processes were observed. In 10 % 1,4‐dioxane/H2O the only product formed was 2,4,6‐trinitrophenol (4), whereas in 60 % 1,4‐dioxane/H2O a mixture of 4 and 5,7‐dinitro‐2‐propyl‐1H‐benzimidazole 3‐oxide (5) was observed in ratios that depend on the HO– concentration. A mechanism involving the formation of σ complexes through the addition of one or two HO– anions to unsubstituted ring positions is proposed for 2,4,6‐trinitrophenol formation. The presence of these complexes was confirmed by NMR studies in 60 % [D8]1,4‐dioxane/D2O. The mechanism suggested for the formation of the N‐oxide includes the cyclization of an N‐alkylidene‐2‐nitrosoaniline‐type intermediate as the rate‐determining step. The decrease in solvent polarity produces a decrease in the observed rate constant for the formation of 4 of about one order of magnitude making the cyclization reaction a competitive pathway. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Amines as leaving groups in nucleophilic aromatic substitution reactions. Part 4.1 σ-Adduct formation in the hydrolysis of 1-amino-2,4,6-trinitrobenzenes

Buján

Remedi

Rossi

2000

J. Chem. Soc., Perkin Trans. 2

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The kinetic study of the reaction of 2,4,6-trinitro-1-pyrrolidinobenzene 3, 2,4,6-trinitro-1-piperidinobenzene 1 and 1-morpholino-2,4,6-trinitrobenzene 2 was made in 1,4-dioxane-water mixtures at 25 ЊC. In all cases, several processes were observed, the slowest of them leading to the formation of picrate ion. The fastest processes involved the formation of σ complexes by addition of one or two HO Ϫ to unsubstituted ring positions and the ionisation of the 1 : 1 complex. Besides, for compounds 1 and 3, cis-trans isomerisation of 1 : 2 complexes was kinetically detected. Substitution occurred by displacement of the amino group on the substrate and the 1 : 1 complex. The reaction pathway for the formation of phenol which involves the formation of these complexes has lower energy than that which results from addition to the 1 position of the substrate.

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Structural and spectroscopic investigation of 1-amino-2,4-dinitrobenzenes

Cited by 5 publications

References 21 publications

Preparação de N-alquil derivados do 1-bromo-2,4-dinitrobenzeno e do 1-cloro-2-nitrobenzeno: Uma alternativa às aulas práticas de substituição nucleofílica aromática

Preparação de N-alquil derivados do 1-bromo-2,4-dinitrobenzeno e do 1-cloro-2-nitrobenzeno: Uma alternativa às aulas práticas de substituição nucleofílica aromática

Medium Effect on the Reaction of N‐Butyl‐2,4,6‐trinitroaniline with NaOH

Amines as leaving groups in nucleophilic aromatic substitution reactions. Part 4.1 σ-Adduct formation in the hydrolysis of 1-amino-2,4,6-trinitrobenzenes

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