The Chemistry of the Perfluoro Acids and their Derivatives. V. Perfluoropropionic Acid

Husted, Donald R.; Ahlbrecht, Arthur H.

doi:10.1021/ja01103a026

Cited by 28 publications

(7 citation statements)

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“…To challenge the putative transformation, the simple mono-substituted alkyne 1 with one electron-withdrawing CO 2 Me-group (EWG) was selected. A mixture of alkyne 1 , C 2 F 5 CH 2 NH 2 ·HCl (1.0 equiv) [ 48 ] and NaNO 2 (2.0 equiv) in water/dichloromethane was stirred at room temperature. After 10 min the organic layer became yellow indicating the formation of C 2 F 5 CHN 2 .…”

Section: Resultsmentioning

confidence: 99%

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

Mykhailiuk¹

2015

Beilstein J. Org. Chem.

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SummaryA one-pot reaction between C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes gives C2F5-substituted pyrazoles in excellent yields. The transformation smoothly proceeds in dichloromethane/water, tolerates the presence of air, and requires no purification of products by column chromatography. Mechanistically, C2F5CH2NH2·HCl and NaNO2 react first in water to generate C2F5CHN2, that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane.

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Section: Resultsmentioning

confidence: 99%

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

Mykhailiuk¹

2015

Beilstein J. Org. Chem.

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“…Subsequently, Carreira and colleagues used this methodology to synthesize trifluoromethyldiazomethane and applied this reagent to several reactions 21. 22 Because the electronic properties of the C 2 F 5 and CF 3 groups are similar,1a I considered that the previously unreported reagent C 2 F 5 CHN 2 could be synthesized by diazotization of C 2 F 5 CH 2 NH 2 ⋅ HCl 23…”

Section: Resultsmentioning

confidence: 99%

“…[21,22] Because the electronic properties of the C 2 F 5 and CF 3 groups are similar, [1a] I considered that the previously unreported reagent C 2 F 5 CHN 2 could be synthesized by diazotization of C 2 F 5 CH 2 NH 2 ·HCl. [23] Diazoalkanes react rapidly with alkenes that contain EWGs. [16b, d] Therefore, the active alkene 1 with two EWGs was selected to trap the putative species C 2 F 5 CHN 2 .…”

Section: Resultsmentioning

confidence: 99%

“…Next, the steric requirements of the reaction were investigated. Diverse di-and tri-substituted alkenes (19)(20)(21)(22)(23)(24)(25)(26)(27)(28) with at least one strong EWG (ÀCO 2 R (R= alkyl) or ÀCOMe) were selected ( Table 4). The 1,1-disubstituted substrates smoothly gave the corresponding 1 D-pyrazolines 19 a-22 a, irrespective of the electronic nature of the second substituent ( Table 4, entries 1-4).…”

Section: Resultsmentioning

confidence: 99%

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Generation of C₂F₅CHN₂ In Situ and Its First Reaction: [3+2] Cycloaddition with Alkenes

Mykhailiuk

2014

Chemistry A European J

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“…Acid anhydrides can be prepared by distillation of the acids from phosphorus pentoxide. The amides are readily prepared by the ammonolysis of the acid halides, anhydrides, or esters and can be dehydrated to the corresponding nitriles (31).…”

Section: Derivativesmentioning

confidence: 99%

Fluorinated Higher Carboxylic Acids

Savu

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Perfluorinated carboxylic acids are corrosive liquids or solids. The acids are completely ionized in water. The acids are of commercial significance because of their unusual acid strength, chemical stability, high surface activity, and salt solubility characteristics. The higher members of the series have the property of decreasing the surface tension of aqueous solutions well below the point possible with any type of hydrocarbon surfactant. There are five methods for the preparation of long‐chain perfluorinated carboxylic acids and derivatives: electrochemical fluorination, direct fluorination, telomerization of tetrafluoroethylene, oligomerization of hexafluoropropylene oxide, and photooxidation of tetrafluoroethylene and hexafluoropropylene. In general, the reactions of the perfluoroacids are similar to those of the hydrocarbon acids, although in some cases the electronegativity of the perfluoroalkyl groups make formation of certain derivatives easier or harder. A general summary of formation and properties of the derivatives of perfluorinated acids is discussed. Data on the fluorinated dicarboxylic acids and their derivatives are also summarized.

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The Chemistry of the Perfluoro Acids and their Derivatives. V. Perfluoropropionic Acid

Cited by 28 publications

References 1 publication

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

Generation of C₂F₅CHN₂ In Situ and Its First Reaction: [3+2] Cycloaddition with Alkenes

Fluorinated Higher Carboxylic Acids

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The Chemistry of the Perfluoro Acids and their Derivatives. V. Perfluoropropionic Acid

Cited by 28 publications

References 1 publication

Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes

Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes

Generation of C2F5CHN2 In Situ and Its First Reaction: [3+2] Cycloaddition with Alkenes

Fluorinated Higher Carboxylic Acids

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Product

Resources

About

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

Three-component synthesis of C₂F₅-substituted pyrazoles from C₂F₅CH₂NH₂·HCl, NaNO₂ and electron-deficient alkynes

Generation of C₂F₅CHN₂ In Situ and Its First Reaction: [3+2] Cycloaddition with Alkenes