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텍실에톡시보란에 의한 대표적인 작용기를 가진 유기화합물의 선택환원
차진순 嶺南大學校 基礎科學硏究所 1996 基礎科學硏究 Vol.16 No.-
The approximate rates and stoicchiometries of the reaction of thexylethoxyborane (ThxBHOEt) with selected organic compounds containing representative functional groups were examined in order to define the characteristics of the reagent for selective reductions. The reducing ability ThxBHOEt was also compared with those of the parent thxylborane (ThxBH₂) and appears to be milder than ThxBH₂. ThxBHOEt shows a unique reducing characteristics. Thus, 1-hexanol and ?-hexylamine evolved hydrogen slowly. whereas 1-hexanethiol was absolutely stable. ThxBHOEt reduced aldehydes and ketones slowly to the corresponding alcohols. Carboxylic acids and acid chlorides were converted to the corresponding aldehydes. Finally, nitriles, aromatic ester, epoxides, and sulfides were essentially inert to ThxBHOEt.
차진순 조선대학교 기초과학연구원 2012 조선자연과학논문집 Vol.5 No.2
Some recommended procedures for obtaining aldehydes from carboxylic acid itself and its derivatives, which have been developed in relatively recent years, are summarized. Such procedures should provide a new practical methodology to synthesize the desired aldehyde products in high yields.
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.
Diisobutylchloroalane 에 의한 카르보닐 화합물의 선택환원
車震淳 嶺南大學校 基礎科學硏究所 1994 基礎科學硏究 Vol.14 No.-
Conjugated aldehydes and ketones are reduced rapidly and quantitatively to the corresponding allylic alcohols by diisobutylchloroalane in ether in excellent purities. Even cyclic enones, such as 2-cyclohexenone and 2-cyclopentenone, are reduced cleanly to the desired allylic alcohols without concomitant attack at the double bonds. What is more, chemoselective reduction of aldehydes to primary alcohols in the presence of ketones by diisobutylchloroalane affords an important methodology in organic synthesis.
차진순 嶺南大學校基礎科學硏究所 2001 基礎科學硏究 Vol.21 No.-
A new class of reducing agent, triisopropoxyborane is readily prepared by treating three equivalents of isopropyl alcohol with borane solution(BH_3-THF) at 0 ℃ or 25 ℃ and its reducing characteristics toward selected organic compounds containing representative functional groups was examined. By the use of triisopropoxyborane, ketones, aldehydes as well as epoxides could be reduced satisfactorily, the acetone formed being removed from the equilibrium mixture by stream of dry nitrogen. This mild and specific reduction method agent may occur via the Meerwein-Ponndorf-Verley reduction. Most aliphatic aldehydes and ketones were reduced rapidly to the corresponding alcohols. In addition, aromatic epoxides examined were readily reduced to the corresponding primary alcohols. Triisopropoxyborane provides a highly convenient and selective method for converting a wide variety of organic functionalities to the useful other organic functions.
트리스디에틸아미노수소화알루미늄 리튬에 의한 에스테르의 알데히드로의 부분환원
차진순 嶺南大學校 基礎科學硏究所 1991 基礎科學硏究 Vol.11 No.-
Both aliphatic and aromatic carboxylic esters are readily reduced to the corresponding aldehydes by lithium tris(diethylamino)aluminum hydride in tetrahydrofuran in high yields at -78℃.
Selective Reduction of Organic Compounds with Al-Methanesulfonyldiisobutylalane
차진순,Minyeong Noh 대한화학회 2010 Bulletin of the Korean Chemical Society Vol.31 No.4
The new MPV type reagent, Al-methanesulfonyldiisobutylalane (DIBAO3SCH3), has been prepared and its 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 high selectivity in organic synthesis. In general, the reagent is extremely mild, showing only reactivity toward aldehydes, ketones and epoxides. The reagent exhibits a unique reducing applicability in organic synthesis. Thus, the reagent can achieve a clean 1,2-reduction of α,β-unsaturated aldehydes and ketones to produce the corresponding allylic alcohols in 100% purity. In addition, the reagent shows an excellent regioselectivity in the ring-opening reaction of epoxides. Finally, DIBAO3SCH3 shows a high stereoselectivity in the reduction of cyclic ketones to produce the thermodynamically more stable epimers exclusively.