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Reaction of Potassium 9-sec-Amyl-9-boratabicylco[3.3.1]nonane with Selected Organic Compounds Containing Representative Functional Groups
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  • Reaction of Potassium 9-sec-Amyl-9-boratabicylco[3.3.1]nonane with Selected Organic Compounds Containing Representative Functional Groups
  • Reaction of Potassium 9-sec-Amyl-9-boratabicylco[3.3.1]nonane with Selected Organic Compounds Containing Representative Functional Groups
저자명
차진순,윤말숙,이광우,이재철,Cha. Jin Soon,Yoon. Mal Sook,Lee. Kwang Woo,Lee. Jae Cheol
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1989년|10권 1호|pp.75-80 (6 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

The approximate rates and stoichiometry of the reaction of excess potassium 9-sec-amyl-9-boratabicylco[3.3.1]nonane (K 9-sec-Am-9-BBNH) with selected organic compounds containing representative functional goups under standardized conditions (tetrahydrofuran, $0^{circ}C)$ were examined in order to explore the reducing characteristics of the reagent for selective reductions. The reagent readily reduces aldehydes, ketones, acid chlorides and epoxides to the corresponding alcohols. However, carboxylic acid, aliphatic nitriles, t-amides, and some sulfur compounds show very little reactivity or no reactivity to this reagent. The most interesting feature of the reagent is that aromatic nitriles are reduced moderately to the corresponding aldehyde stage, wheras aliphatic nitriles are inert. In addition, the reagent shows a high stereoselectivity toward cyclic ketones at $0^{circ}C$ and - $25^{circ}C.$ The selectivity exhibited at $0^{circ}C$ is comparable to that by lithium trisiamylborohydride at that temperature.