Reaction of Potassium Fluoride with Organic Halogen Compounds. (Part I) Reactions of Potassium Fluoride with Organic Halides, Acids, and Esters in presence of Dimethyl Formamide and their Pyrolytic Decaboxylation in presence of Potassium Fluoride

有機 할로겐 化合物과 弗化加里의 反應 (第1報) 有機 할라이드, 酸 및 에스테르와 弗化加里의 디메칠 호름아마이드 溶媒系反應 및 高溫-脫炭酸-熱分解反應

  • 김유선 (原子力硏究所 化學硏究室)
  • Published : 19630900

Abstract

Reactions between potassium fluoride with organic halogen-containing carboxylic acids in dimethyl formamide solvent gave a decarboxylation reaction for the case of fluoro carboxylic acids of the type of $CF_3\;COOH,\;C_3F_7COOH,\;and\;C_2F_5COOH,$ whereas an additional partial fluorination together with dimerization reaction occurred for the chlorine containing acids of the type of $CH_2ClCOOH,\;CH_3CHClCOOH, \;CHCl_2COOH\;and\;o-Cl-C_6H_4-COOH.$ The phenyl halides showed no reactivity, but the halides with two electron attracting substituents on the benzene ring gave mainly dimerization reaction. The esters and alcohols gave an usual fluorination reaction. The same reactions in absence of the solvent at the elevated temperature increase the yield of the dimerized product and gave the cyclized product, fluorenone, in case of ο-chlorobenzoic acid. It was found that the fluorination usually precede the decarboxylation reaction by checking the stiochemical sequence of reaction. Catalytic influence of potassium fluoride were discussed and the mechanism of the reaction was considered.

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References

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