Reactions of phenoxides with nitro- and halo-substituted phthalimides

Williams, Frank J.; Donahue, P. E.

doi:10.1021/jo00441a020

Cited by 106 publications

(40 citation statements)

References 6 publications

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“…A limited number of such polymers have been prepared previously [2,[24][25][26][27]. In a companion study, we explored further the comparison of polymers with such structures [28].…”

Section: Introductionmentioning

confidence: 99%

A comparison of poly(ether imide)s from diamines with 2-aminophenoxy or 4-aminophenoxy units: Synthesis, characterization and properties

Adia

Butler

Eastmond

2006

Polymer

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“…A limited number of such polymers have been prepared previously [2,[24][25][26][27]. In a companion study, we explored further the comparison of polymers with such structures [28].…”

Section: Introductionmentioning

confidence: 99%

A comparison of poly(ether imide)s from diamines with 2-aminophenoxy or 4-aminophenoxy units: Synthesis, characterization and properties

Adia

Butler

Eastmond

2006

Polymer

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“…These conditions implied that the concentration ratio of the products is directly proportional to the ratio of the second-order rate constants for each reaction [32].…”

Section: Methodsmentioning

confidence: 99%

Enthalpy-entropy correlations in reactions of 2,4-dinitrophenyl benzoate with phenols in the presence of potassium hydrogen carbonate and with potassium phenoxides in dimethylformamide

Khalfina

Vlasov

2011

Russ J Org Chem

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Temperature dependences of the relative reactivity of substituted phenols RC 6 H 4 OH in the presence of potassium hydrogen carbonate and of potassium phenoxides RC 6 H 4 O -K + toward 2,4-dinitrophenyl benzoate in dimethylformamide were studied using the competitive reactions technique. Correlation analysis of the relative rate constants k R /k H and differences in the activation parameters (∆∆H ≠ and ∆∆S ≠ ) of competitive reactions revealed the existence of two isokinetic series for each type of nucleophiles. The mechanism of transesterification was interpreted in terms of an approach based on analysis of the effect of substituent in the nucleophile on the activation parameters.

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“…The method using aqueous NaOH rather than sodium methoxide as the base was beneficial from the industrial production of 6F-sodium salt. In general, 17 the nitro groups in 4-nitrophthalimides are displaced by phenoxide about six and nine times faster than the corresponding fluorine, which reacted approximately four times faster than the chloro derivative in the phthalimide. 2,2-Bis[N-phenyl-4-(3,4-dicarboxyphenoxy)phenyl] hexafluoropropane (6F-diimide 3) was synthesized by reacting N-phenyl-4-nitrophthalimide 1 and 6F-sodium salt 2.…”

Section: Synthesis Of Monomermentioning

confidence: 95%

Preparation and properties of soluble aromatic polyetherimides based on 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane dianhydride

Lee

Koo

Kim

et al. 2000

J. Appl. Polym. Sci.

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Aromatic polyetherimides were synthesized from a fluorine containing aromatic carboxylic acid dianhydride, 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]-hexafluoropropane dianhydride (6F-BABPA) and five typical aromatic diamines including 1,1-bis(4-aminophenyl)-1-phenyl-2,2,2-trifluoroethane (3F-DAM) by two-step procedures-amidation to polyamic acids (PAA), followed by thermal imidization of PAA. The chemical and physical properties of the newly prepared polyetherimides (PEI) were compared in terms of their chemical structures, inherent viscosities, mechanical, and thermal properties. All polyetherimides were well soluble in common organic solvents such as N-methyl-2-pyrolidone (NMP), N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), pyridine, and methylene chloride. A PEI prepared from 6F-BABPA/3F-DAM was especially easily dissolved in NMP. The glass transition temperature (T g ) range of the obtained PEI was 209 -257°C. The dielectric constants and refractive index were 2.8 -3.2 and 1.61-1.56, respectively. The polyetherimide, 6F-BABPA/BAPP, with a low fluorine content (11.4% fluorine content), has 0.99% water absorption, whereas the polyetherimide, 6F-BABPA/4-BDAP, having a high fluorine content (26.0% fluorine content) showed 0.35% of water absorption.

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Reactions of phenoxides with nitro- and halo-substituted phthalimides

Cited by 106 publications

References 6 publications

A comparison of poly(ether imide)s from diamines with 2-aminophenoxy or 4-aminophenoxy units: Synthesis, characterization and properties

A comparison of poly(ether imide)s from diamines with 2-aminophenoxy or 4-aminophenoxy units: Synthesis, characterization and properties

Enthalpy-entropy correlations in reactions of 2,4-dinitrophenyl benzoate with phenols in the presence of potassium hydrogen carbonate and with potassium phenoxides in dimethylformamide

Preparation and properties of soluble aromatic polyetherimides based on 2,2-bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane dianhydride

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