Bromation régiosélective en série aromatique. I: Monobromation en position <i>para</i> de phénols et d'aminés aromatiques par le tribromure de tétrabutylammonium

Berthelot, Jacques; Guette, Catherine; Desbène, P.L.; Basselier, Jean-Jacques; Chaquin, Patrick; Masure, D.

doi:10.1139/v89-320

Cited by 45 publications

(21 citation statements)

References 5 publications

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“…The compound 4-bromo-2-methoxyphenol was prepared according to the procedures of Berthelot et al (1989). A mixture of 4-bromo-2-methoxyphenol (0.352 g, 1.736 mmol), benzyl bromide (0.312 g, 1.82 mmol), and powdered K 2 CO 3 (0.26 g, 1.91 mmol) in acetone (5 ml) was stirred and refluxed overnight.…”

Section: -Benzyloxy-4-bromo-2-methoxybenzenementioning

confidence: 99%

Neolignan Skeletons and Benzodioxanes Through Chiral Aryl Alkyl Ether Formation

Li¹,

Helm²

2000

Holzforschung

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Several chiral neolignan skeletons and a benzodioxane were prepared from a tartrate derivative with the crucial chiral aryl alkyl ether formation being accomplished with cesium phenolate and 18-crown-6. These compounds have greater than 96 % enantiomeric excess, and this work represents the first successful synthetic preparation of optically active 8-O-4' type neolignan skeletons. The chiral aryl alkyl ethers were also synthesized from several protected carbohydrates, which can serve as chiral auxiliaries for a wide variety of target molecules.

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Section: -Benzyloxy-4-bromo-2-methoxybenzenementioning

confidence: 99%

Neolignan Skeletons and Benzodioxanes Through Chiral Aryl Alkyl Ether Formation

Li¹,

Helm²

2000

Holzforschung

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“…These doped samples were pressed into pellets at about 2 Â 10 8 Pa. From the pellet, a bar is obtained by cutting the pellet, and carbon paste was put at both ends of the bar to measure the electrical conductivity. Bis (1,5-cyclooctadiene) 9 4,4 0 -dibromodiphenylamine (DPA-Br 2 ), 10 and N-hexyl-4,4 0 -dibromodiphenylamine (N-Hex-DPA-Br 2 ) 7b were prepared according to the literature.…”

Section: Materials and Measurementsmentioning

confidence: 99%

Synthesis and Chemical Properties of Poly(N-substituted diphenylamine-4,4′-diyl)s

2009

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A series of poly(diphenylamine)s with substituents at the N-position, (C 6 H 4 -p-NR-C 6 H 4 -p) n (R = methyl, butyl, hexyl, and benzoyl), were prepared by organometallic polycondensation using a zerovalent nickel complex. These polymers were soluble in organic solvents such as THF, N-methylpyrrolidone (NMP), and trifluoroacetic acid (TFA), and gave intrinsic viscosity of 0.52-0.93 dL g À1 . They showed number average molecular weights (M n ) of 3400-6100 with M w =M n (M w = weight average molecular weight) of 1.9-2.4 in GPC analysis. The polymers exhibited photoluminescence (PL) with emission peaks at EM ¼ 408{425 nm in NMP solutions. P(DPA)-Ni had chemical properties different from those of P(DPA)-Ox, which was prepared by oxidative polymerization of C 6 H 5 NHC 6 H 5 . 6a P(DPA)-Ni is considered to have a welldefined linear structure shown in eq 1, because the Ni(0)L m promoted polycondensation occurs selectively at the C-Br bond.5c On the other hand, P(DPA)-Ox seems to contain structural irregularities because the oxidative polymerization can take place at various C-H positions of the phenyl group and at the NH group. P(DPA)-Ox was considered to contain at least two isomeric units, -C 6 H 4 -NH-C 6 H 4 -and -C 6 H 4 -N(C 6 H 5 )-, in the polymer main chain.

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“…On the other hand, tetra-n-butylammonium tribromide, known to easily brominate phenols at the ortho position, failed to give 3 efficiently. [18] The rate of reaction was too low. After 4 d, at room temperature, only 65 % of bromoanisole 3 was formed according to NMR spectroscopic analysis of the reaction mixture.…”

Section: Synthesis Of Boronic Estermentioning

confidence: 99%

Syntheses of Sterically Hindered Zwitterionic Pyridinium Phenolates as Model Compounds in Nonlinear Optics

et al. 2008

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Pyridinium phenolates possess a dissymmetric delocalised π-electron system providing a huge quadratic nonlinearity. They are a promising class of molecules for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds. The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates 2a-e bearing two tert-butyl substituents

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Bromation régiosélective en série aromatique. I: Monobromation en position para de phénols et d'aminés aromatiques par le tribromure de tétrabutylammonium

Cited by 45 publications

References 5 publications

Neolignan Skeletons and Benzodioxanes Through Chiral Aryl Alkyl Ether Formation

Neolignan Skeletons and Benzodioxanes Through Chiral Aryl Alkyl Ether Formation

Synthesis and Chemical Properties of Poly(N-substituted diphenylamine-4,4′-diyl)s

Syntheses of Sterically Hindered Zwitterionic Pyridinium Phenolates as Model Compounds in Nonlinear Optics

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