A comparative study of anodic fluorination of N-alkyl and N,N-dialkyl phenylacetamides in Et3N 4HF medium
IR@CECRI: CSIR-Central Electrochemical Research Institute, Karaikudi
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| Title |
A comparative study of anodic fluorination of N-alkyl and N,N-dialkyl
phenylacetamides in Et3N 4HF medium
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| Creator |
Ilayaraja, M.
Noel, M. |
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| Subject |
Electroorganic
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| Description |
Anodic fluorination of N-alkyl and N,N-dialkyl phenylacetamides (alkyl = methyl, ethyl, propyl and nbutyl)
was carried out in Et3N 4HF medium. Effects of current density, quantity of electric charge and
alkyl chain length on the overall conversion efficiency and selectivity of fluorinated products are
reported. 1H NMR, 19F NMR and GC/MS were employed for product identification and characterization.
Under galvanostatic condition, N-alkyl phenylacetamides lead to predominantly monofluoro derivative
at ortho position in the aromatic ring. Mono and difluoro active methylene derivatives and p-fluoro
compounds were also formed in smaller quantities. The selectivity was low in the case of N,N-dialkyl
phenylacetamides. On increasing the electricity passed beyond 2 F/mol, the o-fluoro compound produced
1,4 addition compounds followed by further chemical and electrochemical transformations. Cyclic voltammetric
studies indicated significant adsorption of N,N-dialkyl compounds. Potentiostatic electrolysis
lead to predominantly side chain fluorination at the active methylene group. The product distribution
under different experimental conditions is explained on the basis of reactant adsorption and protonation
at the amide group.
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| Publisher |
Elsevier B.V.
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| Date |
2009
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://cecri.csircentral.net/435/1/093-2009.pdf
Ilayaraja, M. and Noel, M. (2009) A comparative study of anodic fluorination of N-alkyl and N,N-dialkyl phenylacetamides in Et3N 4HF medium. Journal of Electroanalytical Chemistry, 632 (1-2). pp. 45-54. ISSN 1572-6657 |
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| Relation |
http://cecri.csircentral.net/435/
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