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Reaction of Dipyrrolidinoaluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups
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  • Reaction of Dipyrrolidinoaluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups
  • Reaction of Dipyrrolidinoaluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups
저자명
Cha. Jin Soon,Kwon. Oh Oun,Kim. Jong Mi,Lee. Jae Cheol
간행물명
Bulletin of the Korean Chemical Society
권/호정보
1994년|15권 8호|pp.644-649 (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 reaction of excess dipyrrolinoaluminum hydride (DPAH) with selected organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, 0, reagent : compound=4 : 1) were examined in order to define the characteristics of the reagent for selective reductions. The reducing ability of DPAH was also compared with that of bis(diethylamino)aluminum hydride (BEAH). The reagent appears to be stronger than BEAH, but weaker than the parent reagent in reducing strength. DPAH shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, acid chlorides, epoxides, and nitriles readily. In addition to that, ${alpha},;{eta}$-unsaturated aldehyde is reduced to the saturated alcohol. Quinone are reduced cleanly to the corresponding 1,4-reduction products. The examination for possibility of achieving a partial reduction to aldehydes was also performed. Both primary and tertiary aromatic carboxamides are converted to aldehydes with a limiting amount of DPAH. Finally, disulfides and sulfoxides are readily reduced to thiols and sulfides, respectively.