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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 22, Number 1
JKCSEZ 22(1)
February 20, 1978 

 
Title
Effect of Lithium Chloride on the Borane Reduction of Organic Compound

보란-염화리튬에 의한 유기화합물의 환원반응
Author
Nung Min Yoon, Jin Soon Cha

윤능민, 차진순
Keywords
Abstract
BH3-THF 용액에 염화리튬을 가한 새로운 환원계의 환원특성에 대한 연구가 대표적인 작용기를 가진 유기화합물을 가지고 표준조건(0˚, THF)에서 이루어졌다. 조사 연구된 화합물중 벤조페논, 4가지 에스테르 및 시클로헥센은 BH3 환원과 별 차이를 보이지 않았으나, 2-헵탄온, 아세토페논, 염화벤조일, 프탈산무수물, 그리고 3가지 에폭시화물은 소량의 염화리튬에 의해 빠른 속도로 환원이 완결 되었다. 특히 에폭시화시클로헥센의 환원에 있어서는 소량의 염화리튬 존재하에서는 정량적으로 시클로헥산올을 생성하였으나 염화리튬의 양이 증가하면 2-클로로시클로헥산올이 시클로헥산올과 함께 생성됨을 알았다. 또한, 에폭시화시클로헥센과의 반응에 있어서 질산리튬은 염화리튬과는 달리 별로 효과가 없었다. 따라서 보란-염화리튬용액에 클로로수소화붕소리튬의 생성가능성을 논의하였다.

The effect of lithium chloride on the borane reduction of organic compounds was studied for three ketones, seven acid derivatives, three epoxides and cyclohexene in tetrahydrofuran at 0˚. When compared with borane itself, borane-lithium chloride system enhanced the rates of reductions markedly of 2-heptanone, acetophenone, benzoyl chloride, phthalic anhydride, and three epoxides, whereas the reductions of benzophenone, four esters and cyclohexene showed little or no effect. BH3-LiCl (1 : 0.1) reduced styrene oxide in 2 hr at 0˚ to give 94.2 % yield of alcohols, 1-to 2-phenylethanol ratio being 60.8 to 39.2. And in the reduction of cyclohexene oxide, BH3-LiCl (1 : 0.1) gave a quantitative yield of cyclohexanol in 2 hr at 0˚, however BH3-LiCl (1 : 1) gave 58 % cyclohexanol and 42 % 2-chlorocyclohexanol. In the reduction of cyclohexene oxide, lithium nitrate showed no rate enhancement even when the salt was added in large excess. A formation of lithium chloroborohydride in the BH3-LiCl system is suggested.

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