• Bulletin of the Korean Chemical Society
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• 제32권8호
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• pp.2525-2526
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• 2011

• Bulletin of the Korean Chemical Society
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• 제30권12호
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• pp.3120-3122
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• 2009

• 대한화학회지
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• 제26권5호
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• pp.340-348
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• 1982

술폭시화물을 보란으로 환원할 때 붕산트리페닐을 촉매량(10몰 퍼센트) 가하면 대응하는 황화물로 환원이 현저히 촉진됨이 관찰되어 이 환원계에 의해 구조적으로 서로 다른 몇가지 술폭시화물의 환원반응이 조사되었다. 술폭시화 테트라메틸렌은 5분 이내(보란만으로는 24시간 걸림) 술폭시화 디에틸, 술폭시화 디벤질, 술폭시화 벤질페닐은 1시간내에 정량적으로 환원이 완결되었으며 술폭시화 디페닐은 반응이 느려서 24시간에 90% 수율(보란만으로는 24시간에 18% 수율)로 환원되었다. 삼플루오르화붕소 에틸에테르 및 붕산트리에틸의 촉매효과는 붕산트리페닐보다 덜하였다.

• Bulletin of the Korean Chemical Society
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• 제25권3호
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• pp.341-342
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• 2004

• 대한화학회지
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• 제31권2호
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• pp.197-202
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• 1987

cis 및 trans 2-methyl-N-phenyl-1,3-oxathiolane-2-acetamide (b) 및 (c)의 sigmatropic rearrangement에 의하여 생성되는 각각의 sulfenic acid (d) 및 (f)는 deuterium exchange reaction에 의하여 확인되었다. cis와 sulfoxide (b)와 (c)의 이성질화가 중성조건하에서는 일어나지 않으나, 산성촉매 존재하에서는 일어난다는 것이 발견되었다. 중성조건하에서 이성질화가 일어나지 않는 것은 sulfenic acid의 SOH 산소원자와 NH proton 사이의 수소결합이 관여하는 stereospecific recyclization에 기인하거나 기하학적 요구에 기인한다고 설명된다. 한편 cis sulfoxide (b)와 trans sulfoxide (c)의 혼합물을 주는 전구물질 1, 3-oxathiolane의 산화반응에서 benzene seleninic acid를 촉매로 하는 $H_2O_2$의 산화에 의하여 cis sulfoxide (b)가 높은 수율로 선택적으로 얻어졌다.

• 대한화학회지
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• 제27권6호
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• pp.434-440
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• 1983

테트라히드로프란 용액에서 수소화붕소나트륨과 붕산트리페닐을 사용해서 카르복시산, 카르복시산염, 3차아미드 및 술폭시드를 환원하는 새로운 방법을 개발하였다. 즉 카르복시산은 실온에서 6~12시간에 정량적으로 환원될 수 있으며, 지방족 카르복시산염은 실온에서 6시간에 정량적으로 환원되나 방향족 산염은 $65^{\circ}C$에서 24시간이 소요되었다. 3차 아미드는 실온에서 3~6시간에 88∼100%의 좋은 수율로 환원되었으며, 조사한 대부분의 술폭시드는 실온에서 1~6시간에 98∼100%의 수율로 환원되었으나, 디페닐술폭시드는 보다 격렬한 조건에서 48시간에 환원할 수 있었다.

• Bulletin of the Korean Chemical Society
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• 제33권1호
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• pp.35-38
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• 2012

Room temperature oxidation of organic sulfides with polyvinylpyrrolidone-supported hydrogen peroxide (PVP-$H_2O_2$) in the presence of Mn(III) complexes of meso-tetraphenylporphyrin, Mn(TPP)X (X = OCN, SCN, OAc, Cl) and imidazole (ImH) leads to the highly chemoselective (ca. 90%) oxidation of sulfides to the corresponding sulfoxide. The efficiency of reaction has been shown to be influenced by different reaction parameters such as the nature of counterion (X) and solvent as well as the molar ratio of reactants. Using Mn(TPP)OCN and ImH in 1:15 molar ratio and acetone as the solvent leads to the efficient oxidation of different sulfides.

• Bulletin of the Korean Chemical Society
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• 제12권6호
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• pp.612-617
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• 1991

The approximate rates and stoichiometry of the reaction of excess 1,3,2-biphenyldioxaborepin [2,2'-biphenoxyborane (BPB)] with selected organic compounds containing representative functional groups under the standardized conditions (tetrahydrofuran, hydride to compound being 4 : 1, room temperature) was examined in order to define the characteristics of the reagent for selective reductions and compare its reducing power with those of other substituted boranes. The results indicate that BPB is unique and the reducing power is much stronger than that of other dialkoxyboranes, such as catecholborane and di-s-butoxyborane. BPB reduces aldehydes, ketones, quinones, lactones, tertiary amides, and sulfoxides readily. Carboxylic acids, anhydrides, esters, and nitriles are also reduced slowly. However, the reactions of acid chlorides, epoxides, primary amides, nitro compounds, and disulfides with this reagent proceed only sluggishly.

• Bulletin of the Korean Chemical Society
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• 제12권6호
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• pp.644-649
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• 1991

The approximate rates and stoichiometry of the reaction of excess lithium tris(dibutylamino)aluminum hydride (LT-DBA) with selected organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, $0^{\circ}C$) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of LTDBA was also compared with those of the parent lithium aluminum hydride and the alkoxy derivatives. The reagent appears to be much milder than the parent reagent, but stronger than lithium tri-t-butoxyaluminohydride in reducing strength. LTDBA shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, acid chlorides, epoxides, and amides readily. In addition to that, ${\alpha},{\beta}$-unsaturated aldehyde is reduced to ${\alpha},{\beta}$-unsaturated alcohol. Quinones are reduced to the corresponding diols without evolution of hydrogen. Tertiary amides and aromatic nitriles are converted to aldehydes with a limiting amount of LTDBA. Finally, disulfides and sulfoxides are readily reduced to thiols and sulfides, respectively, without hydrogen evolution.

• Bulletin of the Korean Chemical Society
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• 제15권8호
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• pp.644-649
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• 1994

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, ${\alpha},\;{\beta}$-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.