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尹末淑,金永植,車震淳 嶺南大學校附設 基礎科學硏究所 1986 基礎科學硏究 Vol.6 No.-
A systematic study on the reaction of the lithium-borane system in tetrahydrofuran with representative organic compounds under standardized conditions (THF, 0℃, H?/compd=4/1) has been carried out in order to characterize the reducing characteristics and entity of this reducing system. Most aldehydes and ketones are reduced rapidly to the alcohol stage. Carboxylic acids and acid chlorides are rapidly reduced to corresponding alcohol stages are reduced only slowly. Nitro compounds are very slowly reduced and sulfur compounds are essentially inert to this reducing system. Consequently, this system possesses both reducing characterictics of borane, an acidic type, and lithium borohydride, a basic type.
차진순,윤말숙,이광우,이재철,Cha Jin Soon,Yoon Mal Sook,Lee Kwang Woo,Lee Jae Cheol Korean Chemical Society 1989 Bulletin of the Korean Chemical Society Vol.10 No.1
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.
텍실브로모보란-메틸 설피드 착물을 이용한 카르복시산의 알데히드로의 부분 환원
차진순,윤말숙,김진억,오세연 嶺南大學校附設 基礎科學硏究所 1985 基礎科學硏究 Vol.5 No.-
The systematic study on the direct partial reduction of carboxylic acids to the corresponding aldehydes with thexylbromoborane-methyl sulfide under the practical conditions (carbon disulfide, room temperature) has been done and also some representative carboxylic acids have been applied to the partial reduction under the optimal reaction condition. The reaction is quite general and the yields of aldehydes are very excellent, especially almost quantitative in aliphaticcarboxylic acids.
Potassium 9-s-Amyl-9-boratabicyclo〔3.3.1〕nonane의 합성과 환원 특성
車震淳,尹末淑,李光雨 嶺南大學校附設 基礎科學硏究所 1987 基礎科學硏究 Vol.7 No.-
A new reducing agent, potassium 9-s-amyl-9-boratabicycol[3. 3. 1]nonane (K0-s-Amyl-9-BBNH) was prepared from the reaction of excess potassium hydride and B-s-amyl-9-BBN, which was synthesized by hydroboratind 2-methyl-2butene with 9-BBN. The reducing charcteristics of the reagent to the repressentative organic compounds have been studied systematically under the standardized conditions (0C, THF, H-/compound=4 : 1). The reagent appeared as a relatively mild selective reducing agent. Thus, aldehydes, ketones, acid chlorides, and epoxides are reduced rapidly to the corresponding alcohol stages, while aromatic amides, aromatic nitriles, and esters are reduced only slowly. In addition to that, it exhibits remarkably high stereoselectivity in the reduction of monocy-clic and bicyclic ketones.
Diisopropoxyborane과 대표적인 니트릴 및 카르복시산 염화물의 반응
車震淳,金鐘大,尹末淑,金進億 嶺南大學校附設 基礎科學硏究所 1982 基礎科學硏究 Vol.2 No.-
The reducing characteristics of diisopropoxyborane were examined for the reaction of it with representative nitriles and acid chlorides in tetrahydrofuran under the various conditions such as the reaction temperature and proportions of reagent or BF₃to the compound. Nitriles were reduced to the amine stage. The rate of reaction of nitriles was faster than that of acid chlorides under same condition. The rate of reaction of acid chlorides was remarkably enhanced as the reaction temperature and the ratio of BF₃or reagent was increased. However, for the purpose of partial reduction of acid chlorides to the corresponding aldehyde, the reaction was carried out under the more drastic reaction condition and in the presence of excess hydride, the resulting aldehyde was shown to be diminished. Especially, the reaction of benzoyl chloride with an equivalent amount of diisopoxyborane yielded 36.2% benzaldehyde at 25℃ in 24 hour.
차진순,오세연,이광우,윤말숙,이재철,Cha Jin Soon,Oh Se Yeon,Lee Kwang Woo,Yoon Mal Sook,Lee Jae Cheol,Kim Jin Euog Korean Chemical Society 1988 Bulletin of the Korean Chemical Society Vol.9 No.1
New methods for the direct reduction of carboxylic acids to aldehydes through the treatments of B-acyloxy-9-borabicyclo[3.3.1]nonane (acyloxy-9-BBN) with tert-butyllithium and 9-borabicyclo[3.3.1]nonane or with lithium 9-boratabicyclo[3.3.1]nonane (Li 9-BBNH) are described. Both these systems provide the corresponding aldehydes from various carboxylic acids in high yields. A mechanism for the recuction through stepwise treatment of acyloxy-9-BBN with tert-butylithium and 9-BBN, which seems to involve the hydride migration through 9-BBN, is proposed and discussed in connection with the reduction through treatment of acyloxy-9-BBN with Li 9-BBNH.