The synthesis of stable perfluoroazidoazomethines and their rearrangement to perfluorodialkylcarbodiimides

Gontar, A. F.; Glotov, E. N.; Vinogradov, A. S.; Bykhovskaya, E. G.; Knunyants, I. L.

doi:10.1007/bf00947743

Cited by 3 publications

(2 citation statements)

References 3 publications

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“…Recently, attention has been paid to new synthesis and application of carbodiimides. For example, Gontar et al synthesized perfluorodialkylcarbodiimides via the rearrangement of perfluoroazidoazomethines (Gontar et al, 1985). Synthesis of other carbodiimides was also reported (Gorbatenko et al, 1984;Matveev et al, 1988;Saito et al, 1992).…”

Section: Introductionmentioning

confidence: 99%

Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media

Nakajima¹,

Ikada²

1995

Bioconjugate Chem.

674

515

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To study the mechanism of amide formation between carboxylic acid and amine in aqueous media using 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (EDC), hydrogels with two different types of carboxyl group locations were employed as substrates containing the carboxylic acid, while ethylenediamine and benzylamine were used as amine. In parallel, a study was undertaken with cyclizable carboxylic acids (maleic acid and poly(acrylic acid) and noncyclizable carboxylic acids (fumaric acid and poly(ethylene glycol) with the terminal carboxyl groups) to assess the reaction products by 13C-NMR and IR. EDC rapidly lost its activity in aqueous media of low pH, producing the corresponding urea derivative, but was very stable at neutral and higher pH regions. EDC could react with carboxyl groups at a relatively narrow low pH range such as 3.5-4.5. If carboxyl groups were cyclizable, they would react quickly with EDC producing carboxylic anhydrides, which formed the corresponding amides when amine compounds were present. On the other hand, a trace of amide was formed in the case of noncyclizable carboxylic acids. In addition, an excess of EDC caused an undesired side reaction to form stable N-acylurea, regardless of the special location of carboxylic acids.

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Section: Introductionmentioning

confidence: 99%

Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media

Nakajima¹,

Ikada²

1995

Bioconjugate Chem.

674

515

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“…Perfluoropropane (13), n-C4F] o (11), the isomeric perfluoropentanes 15a,b and n-perfluorohexane(17) were identified by comparison with authentic samples.General Procedure for the Reaction of Imines with Fluorine Gas. A 100-mL stainless steel reactor, which was briefly passivated with 1 atm of fluorine at 22 °C, was used in all reactions.…”

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confidence: 99%

A novel synthesis of N-fluoroperfluoroalkanimines. Reaction of perfluorinated secondary amines with antimony pentafluoride

Петров¹,

DesMarteau²

1992

Inorg. Chem.

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Perfluorinated secondary amines prepared by the reaction of the corresponding internal azaalkenes with fluorine gas in the presence of a metal fluoride undergo a cleavage reaction with SbF5 at elevated temperatures. The reaction results in the formation of a mixture of perfluoroalkane and iV-fluoroalkanimine. Reaction of (CF3)2CF-N(F)-C2F5 with SbFs is exothermic at 22 °C giving a mixture of C2F6 and perfluoro-2-azabutene-2. An intermediate step of the latter reaction is the isomerization of the 7V-fluoroalkanimine of hexafluoroacetone by SbF5, resulting in the formation of perfluoro-2-azabutene-2.

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The Tautomerism of Heterocycles: Five-membered Rings with Two or More Heteroatoms

Минкин

Гарновский

Elguero

et al. 2000

Advances in Heterocyclic Chemistry

300

175

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The synthesis of stable perfluoroazidoazomethines and their rearrangement to perfluorodialkylcarbodiimides

Cited by 3 publications

References 3 publications

Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media

Mechanism of Amide Formation by Carbodiimide for Bioconjugation in Aqueous Media

A novel synthesis of N-fluoroperfluoroalkanimines. Reaction of perfluorinated secondary amines with antimony pentafluoride

The Tautomerism of Heterocycles: Five-membered Rings with Two or More Heteroatoms

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