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

有機할로겐 化合物과 金屬과의 反應 (第 2 報) 有機亞鉛 클로린콤푸렉쓰 生成에 關한 各種 용매효과

  • Kim, You-Sun (Chemistry Division, Atomic Energy Research Institute)
  • 김유선 (原子力硏究所 化學硏究室)
  • Published : 19650300

Abstract

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.

Keywords

References

  1. Journal of the Korean Chemical Society v.7 Y.S. Kim
  2. Organic Reactions R. Adams(et al.)
  3. J. Am. Chem. Soc. v.80 Glen A. Russel(et al.)
  4. J. Org. Chem. v.28 Glen A. Russel(et al.)
  5. J. Am. Chem. Soc. v.73 G. R. Leader;J. F. Gormley
  6. Organic Reactions v.I R. Adams(et al.)
  7. J. Am. Chem. Soc. v.61 Natelson;Galifried