Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Chlorination of Alcohols Using Potassium Carbonate and Silicon Tetrachloride

탄산칼륨 존재하에서 사염화규소를 이용한 알코올의 염소화반응

  • Ha, Dong Soo (Department of Chemistry, Sunchon National University) ;
  • Kim, Hyeung Ae (Department of Chemistry, Sunchon National University)
  • 하동수 (순천대학교 자연과학대학 화학과) ;
  • 김형애 (순천대학교 자연과학대학 화학과)
  • Published : 19971000
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Abstract

Potassium carbonate reacts with silicon tetrachloride to form trichlorosilyloxy carbonylchloride which reacts subsequently with another molecule of silicon tetrachloride leading to phosgene eventually in chlorinated solvents. This in situ generated trichlorosilyloxy carbonylchloride or phosgene were found to be very effective for the chlorination of a wide variety of alcohols to the corresponding chlorides. Primary, secondary and benzylic alcohols were converted into corresponding chlorides when treated with silicon tetrachloride in the presence of potassium carbonate at room temperature.

탄산칼륨 존재하에서 사염화규소는 1차, 2차, 3차 및 벤질알코올 유도체 뿐 만 아니라 시클로헥산올과 같은 고리형 알코올, 알릴 알코올등의 염소화반응에 효과적임을 알 수 있었다. 탄산칼륨이 사염화규소의 반응성이 큰 규소-염소 결합과 반응하여 생성될 수 있는 불안정한 중간체인 Trichlorosilyloxy carbonylchloride 혹은 최종적으로 평형농도 만큼 소량씩 생성되리라 예상되는 Phosgene은 모두 반응메카니즘적으로 알코올의 염소화반응에 관여할 수 있음을 알았다.

Keywords

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