Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Fast Deoxygenation of Sulfoxides with Borane-Triphenyl Borate (1 : 0.1) System

보란-붕산트리페닐 (1 : 0.1) 계에 의한 술폭시화물의 신속한 탈산소화반응에 관한 연구

  • Byung Tae Cho (Department of Chemistry, College of Science and Technology, Sogang University) ;
  • Nung Min Yoon (Department of Chemistry, College of Science and Technology, Sogang University)
  • 조병태 (서강대학교 이공대학 화학과) ;
  • 윤능민 (서강대학교 이공대학 화학과)
  • Published : 1982.10.30
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Abstract

The presence of 10 mole percent triphenyl borate accelerated dramatically the rate of reduction of structurally different sulfoxides with borane in tetrahydrofuran at room temperature, compared to the slow reduction with borane itself. Tetramethylene sulfoxide underwent complete reduction in 5 min and diethyl sulfoxide, dibenzyl sulfoxide and benzylphenyl sulfoxide were reduced quantitatively within 1h, whereas the reduction of diphenyl sulfoxide was rather slow, giving diphenyl sulfide in 90% yield in 24h. Boron trifluoride etherate and triethyl borate were less effective than triphenyl borate. A possible mechanism is presented.

술폭시화물을 보란으로 환원할 때 붕산트리페닐을 촉매량(10몰 퍼센트) 가하면 대응하는 황화물로 환원이 현저히 촉진됨이 관찰되어 이 환원계에 의해 구조적으로 서로 다른 몇가지 술폭시화물의 환원반응이 조사되었다. 술폭시화 테트라메틸렌은 5분 이내(보란만으로는 24시간 걸림) 술폭시화 디에틸, 술폭시화 디벤질, 술폭시화 벤질페닐은 1시간내에 정량적으로 환원이 완결되었으며 술폭시화 디페닐은 반응이 느려서 24시간에 90% 수율(보란만으로는 24시간에 18% 수율)로 환원되었다. 삼플루오르화붕소 에틸에테르 및 붕산트리에틸의 촉매효과는 붕산트리페닐보다 덜하였다.

Keywords

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