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Jin Soon Cha, Seung Jin Park 조선대학교 기초과학연구원 2009 조선자연과학논문집 Vol.2 No.3
The new MPV-type reagent, Al-fluorodiisobutylalane (DIBAF), has been prepared and their reducing characteristics in the reduction of selected organic compounds containing representative functional groups have been examined in order to find out a new reducing system with unique applicability in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones, and epoxides. The reagent achives a clean 1,2-reduction of enals to the corresponding allylic alcohols in a 100% purity, but shows no reactivity toward enones. The reagent also shows an excellent regioselective cleavage of substituted epoxides. In addition, DIBAF produces the thermodynamically more stable alcohol epimer in high stereoselectivity in the reduction of cyclic ketones
BH₃와 PCC를 이용하여 환원-산화법에 의한 카르복시산 염으로부터 알데히드 합성에 관한 연구
차진순, 이재철 영남대학교 기초과학연구소 2000 基礎科學硏究 Vol.20 No.-
A new convinent conversion of carboxylic acid salts into the corresponding aldehydes by utilizing borane has been devised : the procedure involves the reaction of carboxylic acid salts with borane to form the acyloxyborohydride intermediate, followed by the treatment with dimethyl sulfate to be converted into trialkoxyboroxine. Finally, the boroxine intermediate is converted to aldehydes by oxidation with pyridinium chlorochromate or pyridinium dichromate. The yields of aldehydes by this procedure are very excellent. This method provides one of the most economical procedures reported in the literature.
트리알콕시수소화붕소 리튬의 합성과 그들의 안정성 및 화학
車震淳,金進億,李在哲 嶺南大學校附設 基礎科學硏究所 1984 基礎科學硏究 Vol.4 No.-
The reaction in tetrahydrofuran of potassium trialkoxyborohydrides with lithium chloride was examined in detail to establish the generality of this synthesis of the corresponding lithium trialkoxyborohydrides and the stability of these lithium derivatives in tetraydrofuran was examined using ?? NMR spectroscopy. For R=i-Pr, the lithium salt is very stable. However, R=s-Bu and t-Bu, with increasing steric requirement, the lithium derivatives are unstable and thus dissociated into (RO)BH₃- and (RO)₄B-. The stereoselectivity of lithium triisopropoxyborohydride (LIPBH) on the reduction of cyclic ketones was investigated and compared with that of the potassium derivative.
차진순,이재철 嶺南大學校基礎科學硏究所 1999 基礎科學硏究 Vol.19 No.-
The reducing characteristics of diisobutyldiphenylaminoalane (DIBANPh_2) as selective reducing agent in the reduction of carbonyl compounds, have been studie systematically. Aldehydes are smoothly reduced to the corresponding alcohols by BIBANPh_2 i ether solution.
Lithium Thexyl^t butoxyborohydride의 합성과 새로운 환원특성
차진순, 이재철 영남대학교 기초과학연구소 2000 基礎科學硏究 Vol.20 No.-
The new reducing agent, lithium thexyltbutoxyborohydride was prepared from thexyltbutoxyborane and tert-butyllithium. The reaction of organic compounds possessing representative functional groups with this reagent has been investigated in detail so as to estabilish their usefullness as chremo-, regio-, stereoselective reducing agent in organic synthesis. Thus, we have examined the general reducing pattern of this reagent toward general organic functional groups, such as carbonyl compounds, carboxylic acid derivatives, epoxides, etc. Especially, the stereochemistry in the reduction of cyclic ketones has been examined in detail.
디이소부틸수소화알루미늄=메틸설피드 착물에 의한 니트릴의 알데히드로의 환원
車震淳 嶺南大學校 基礎科學硏究所 1993 基礎科學硏究 Vol.13 No.-
A systematic study of the partial reduction of nitriles to the corresponding aldehydes with diisobutylaluminum hydride-dimethyl sulfide complex under practical conditions has been carried out. The yields of aldehydes are good in the aliphatic and aromatic series.
Diisobutyldiethylaminoalane에 의한 카르보닐 화합물의 선택환원
차진순 嶺南大學校 基礎科學硏究所 1995 基礎科學硏究 Vol.15 No.-
The reducing characteristics of diisobutyldiethylaminoalane, as a chemoselective reducing agent in the reduction of an equimolar amount of different carbonyl compounds, have been examined systematically. Aldehydes are smoothly reduced to alcohols. Furthermore, conjugated aldehydes and ketones are reduced to the corresponding allylic alcohols quantitatively by diisobutyldiethylaminoalane in ether solution with excellent purity.
9-텍실옥실-9보라타비시클로[3. 3. 1]노난 리튬의 합성과 그것의 입체선택환원성
車震淳,金進億,金鍾大 嶺南大學校附設 基礎科學硏究所 1984 基礎科學硏究 Vol.4 No.-
The reaction in tetrahydrofuran of potassium 9-(2,3-dimethyl-2-butoxy)-9-boratabicyclo [3. 3. 1]nonane (K 9-OThx-9-BBNH) with lithium chloride was examined in detail to establish the generality of this synthesis of the corresponding lithium derivatives. This new reagent, Li 9-OThx-9-BBNH, shows an excellent stereoselectivity .in the reduction of cyclic ketones. Especially, the easy removal of the byproduct of the reaction and thus simple isolation procedure provides a major advantage for this reagent.