The Electrochemical Fluorination of N, N-Dimethylalkylamines and N, N-Dialkylmethylamines

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  • N,N-ジメチルアルキルアミンおよびN,N-ジアルキルメチルアミンの電解フッ素化反応
  • N,N ジメチルアルキルアミン オヨビ N,N ジアルキルメチルアミン ノ デ

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Electrochemical fluorination of N, N-dimethylakylamines [(CH3)2NR; R=C2H5 n-C3H7, n-C4H9, n-O5H11, t-C4H9, c-O5H9 and c-C6H11] and N, N-dialkylmeth ylamines [R1R2⋅NCH3; R1=R2=C2H5, R1=R2=n-C3H7, R1=R2=n-C4H9;R1=n-C3H7, R2=n-C4H9 and R1 n-C3H7, R2 =n-C5H11] was carried out.<BR>In the case of N, N-dimethylalkyl amines, yields of perfluoroamines decreased with the increase in the number of carbon atoms of the straight-chain alkyl group due to the cleavage of C-N bond. Isomerization and ring-opening reaction occurred extensively for amines with branched and cycloalkyl groups, respectively.<BR>In the case of N, N-dialkylmethylami nes, it was found that the initial concentration of the amine in anhydrous hydrogen fluoride has great influence upon the yield of the fluorinated amine, which was not the case with N, N-dimethylalkylamines: The higher concentration gave the better results. The β-scission of an alkyl group of amines resulted in the formation of a considerable amount of perfluoro(N, N-dimethylalkylamine). The longer alkyl group in an asymmetric N, N-dialkylmethylamine showed a tendency of such β-scission more easily.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1985 (10), 1980-1987, 1985-10-10

    The Chemical Society of Japan

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