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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 9, Number 1
JKCSEZ 9(1)
February 20, 1965 

 
Title
Reaction of Organic Halogen Compounds with Metals (Part Ⅱ) A Formation of Organic Chlorine Zinc Complex in Various Solvents

유기할로겐 화합물과 금속과의 반응 (제2보) 유기아연 클로린콤푸렉쓰 생성에 관한 각종용매효과
Author
You Sun Kim

김유선
Keywords
Abstract
토루엔, 디메틸폴움아마이드, 디메틸슬포옥사이드, 데트라하이들퓨란, 아세토나이트라일 및 디옥센 등 용매존재하에서 모노클로로초산과 아연을 반응시켜 본 결과, 용매효과를 나타냈었다. 반응시약의 반응도가 극성 및 친수성에 따라 증가하였다. 같은 용매계를 사용하여 에틸모노클로로초산을 반응시켜 본 결과, 용매효과를 나타냈으나 산의 경우보다 그 차가 크지 못하였다. 산, 에스타, 아연 및 카보닐화합물(벤즈알데히드 및 4-헤프타논)의 반응에 있어서는 알데하이드의 경우에 있어서는 Reformatsky 반응생성물을 주었으나, 4-헤프타논과의 반응도는 없었다. 반응생성물의 수률은 시약첨가방법에 따라 변화되었다. 최고수률은 산의 하이드로옥시산(38.5%), 0.8g의 salt(아세트나이트라일용매)이며, 에스타의 경우에는 에틸신나메이트(19.3%), 폴리머(21.6%)이였다. 카보닐화합물의 경우에 있어서는 반응온도에 따라 시약의 반응도의 변화가 있었다. 연구결과를 용매효과에 관련시켜 논의하였으며, 연구방법에 관하여 기술하였다.

Reaction of monochloroacetic acid with zinc in presence of toluene, dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, acetonitrile, and dioxane solvents showed the solvent effect in order of dimethylformamide, dioxane, dimethyl sulfoxide, toluene, acetonitrile, and tetrahydrofuran. The increasing reactivity of the reagents was observed in order of the polarity and hydrophilicity of the solvent. The same reaction of ethyl monochloroacetate in the same series of solvents showed also the solvent effect, but the difference was not large as compared to that of the acid. The reaction of the acid, ester, zinc, and carbonyl precursors such as benzaldehyde and 4-heptanone gave the Reformatsky reaction product in the case of the aldehyde, but the reactivity with 4-heptanone was slight. The yield of the product was varied by the method of addition of reagents. The best yield observed in case of the acid reaction was 38.5% of the hydroxy acid and 0.8g of the salt in presence of acetonitrile and in case of the ester reaction 19.3% of ethyl cinnamate and 21.6% of polymer. The variation of the reactivity of reagents due to the reaction temperature was observed in case of carbonyl reaction. The result was discussed in terms of the solvent effect and the procedures were described.

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