Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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혼합용매에서의 용매화 (제 5 보) : 메탄올-아세톤 혼합용매계에서 tert-Butyl Halides와 1-Adamantyl Tosylate의 가용매 분해반응

  • Ikchoon Lee (Department of Chemistry, Inha University) ;
  • Sang-Mu La (Department of Chemistry, A-Ju University) ;
  • Byung Hoo Kong (Department of Science Education, Chungbuk National University) ;
  • Bon-Su Lee (Department of Chemistry, Inha University) ;
  • Se Chul Sohn (Department of Chemistry, Inha University)
  • 이익춘 (인하대학교 이과대학 화학과) ;
  • 나상무 (아주대학교 이과대학 화학과) ;
  • 공병후 (충북대학교 사대과학교육과) ;
  • 이본수 (인하대학교 이과대학 화학과) ;
  • 손세철 (인하대학교 이과대학 화학과)
  • Published : 1987.02.20
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Abstract

Solvolysis of tert-butyl halides and 1-adamantyl tosylate in methanol-acetone mixtures and solvolysis of tert-butyl bromide in methanol-chloroform mixtures have been studied. Solvent ionizing power of methanol-acetone mixtures were calculated by the Grunwald-Winstein equation and discussed the Y value variation caused by substrate changes. Y values based on 1-adamantyl tosylate is superion to others since it varies in wide range for methanol-acetone mixtures. It was found that the order of electrophilic assistance to leaving group is OTs > Cl > Br > I.

메탄올-아세톤 혼합용매에서 tert-butyl halides와 1-adamantyl tosylate 가용매 분해반응과 메탄올-클로로포름 혼합용매계에서 tert-butyl bromide의 가용매 분해반응을 연구하였다. 메탄올-아세톤 혼합용매의 이온화 능력의 척도를 구하였으며 기질의 변화에 따른 Y값의 변화를 논의하였다. 메탄올-아세톤 혼합용매계의 Y값은 1-adamantyl tosylate를 이용하여 구한 값이 가장 좋은 결과를 줌을 알 수 있었으며 용매에 의한 이탈기의 OTs > Cl > Br > I순서로 커짐을 알 수 있었다.

Keywords

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