• Journal of the Korean Chemical Society
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• v.27 no.6
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• pp.434-440
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• 1983

New procedures for the reduction of carboxylic acids, carboxylic acid salts, tertiary amides, and sulfoxides with sodium borohydride and triphenyl borate in tetrahydrofuran were developed. Thus carboxylic acids were reduced quantitatively in 6∼12 h at $25^{\circ}C$. Alphatic acid salts were quantitatively reduced to the corresponding alcohols in 6h at $25^{\circ}C$ whereas aromatic acid salts required 24h at $65^{\circ}C$. Tertiary amides were reduced to the corresponding amines in 88∼100% yields in 3∼6h at room temperature. Most sulfoxides examined were reduced to the corresponding sulfides in 98∼100% yields in 1∼6h at $25^{\circ}C$ and completely reduced at $65^{\circ}C$; however, diphenyl sulfoxide required 48h in a more vigorous condition.

• Bulletin of the Korean Chemical Society
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• v.32 no.6
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• pp.1808-1846
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• 2011

From 1975 to 2011, for thirty six years, the author and his collaborators have developed a variety of reducing and hydroborating agents, and applied them to organic synthesis, which involves the 1,2-reduction of ${\alpha}$,${\beta}$-unsaturated carbonyl compounds, stereoselective reduction of cycloalkanones, regioselective ring-opening of epoxides, partial reduction of carboxylic acid derivatives to aldehydes, regioselective addition to carbon-carbon multiple bonds, etc. by utilizing metal hydrides and the newly-devised the Meerwein-Ponndorf-Verley (MPV) type reagents. Such developments provide a new synthetic methodology making possible valuable selective reductions and hydroborations, not practical previously.

• Textile Coloration and Finishing
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• v.25 no.4
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• pp.247-253
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• 2013

The enzyme-like catalytic functions of metal complex phthalocyanine derivatives those containing carboxylic acid groups could be applied as odor-removing systems and antibacterial systems. Pyromellitic dianhydride and 4-nitrophthalimide were used as starting material for synthesizing dinitro-tetracarboxylic acid iron phthalocyanine(compound 1). Then diamino-tetracarboxylic phthalocyanine(compound 2) was obtained by reduction of compound 1. For the formation of covalent bond with cellulose fiber, cyanuric chloride was introduced to the amino group of compound 2 by condensation reaction compound 3. The exhaustion method was employed for adsorbing compound 3 on cotton fiber. K/S values of each fabrics were measured by a CCM system and deodorizing rates were tested by a detector tube method for ammonia gas. K/S values of treated cotton fiber with compound 3 were arranged from 2.1 to 4.2 at $90^{\circ}C$ of exhaustion temperature. Deodorizing rates provided result of 81%, 84%, 88%, 91%, by passing time of 30 min, 60 min, 90 min, 120 min, respectively.

• 한국생물공학회:학술대회논문집
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• 2000.04a
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• pp.562-565
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• 2000

pH- and thermo-sensitive hydrogels containing maleilated chitosan(MC) and N-isopropylacrylamide(NIPAAm) were prepared and characterized for their swelling behavior, biodegradability and drug release profiles. The hydrogels exhibited a typical pH-sensitivity due to the carboxylic acid groups of maleilated chitosan. The change of ratio of NIPAAm to MC in weight did not affect on either lower critical solution temperature(LCST) or EWC significantly. The pH sensitivity of the hydrogel, however, depended on the amounts of carboxylic acid groups of MC. MC was degradable up to 80% weight reduction in 2 hours. The in vitro drug relase profiles were established both in buffer solution pH 1.4 and pH 7.4. Only a negligible amount of indomethacin was released at pH 1.4 in 6 hours, while at pH 7.4 more than 90% of the total drug in the hydrogel was gradually released over ca. 5 hours.

• Transactions on Electrical and Electronic Materials
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• v.14 no.3
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• pp.125-129
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• 2013

Composites of platinum and multiwalled carbon nanotubes (MWNTs) were prepared in various reduction conditions and characterized using cyclic voltammetry. The MWNTs were functionalized with carboxylic acid and/or hydroxyl groups in acidic solutions prior to the formation of MWNT-Pt composites. Platinum nanoparticles were deposited onto the chemically-oxidized MWNTs in 1-propanol and 1,3-propanediol. The reduction of Pt precursors in other solutions could induce differences in their morphologies in composite thin films. The morphologies of MWNTs with Pt deposited were dependent on the reduction solutions, and the electrocatalytic activities on alcohols changed accordingly. The electrochemical activities of the as-prepared MWNT-Pt thin films on common alcohols such as methanol and ethanol were investigated.

• Bulletin of the Korean Chemical Society
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• v.13 no.5
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• pp.531-537
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• 1992

The approximate rates and stoichiometry of the reaction of excess potassium 2-thexyl-1,3,2-dioxaborinane hydride(KTDBNH) with 55 selected compounds containing representative functional groups under standardized conditions (tetrahydrofuran, TEX>$0^{\circ}C$, reagent : compound=4 : 1) was examined in order to define the characteristics of the reagent for selective reductions. Benzyl alcohol and phenol evolve hydrogen immediately. However, primary, secondary and tertiary alcohols evolve hydrogen slowly, and the rate of hydrogen evolution is in order of $1^{\circ}$> $2^{\circ}$> $3^{\circ}$. n-Hexylamine is inert toward the reagent, whereas the thiols examined evolve hydrogen rapidly. Aldehydes and ketones are reduced rapidly and quantitatively to give the corresponding alcohols. Cinnamaldehyde is rapidly reduced to cinnamyl alcohol, and further reduction is slow under these conditions. The reaction with p-benzoquinone dose not show a clean reduction, but anthraquinone is cleanly reduced to 9,10-dihydro-9,10-anthracenediol. Carboxylic acids liberate hydrogen immediately, further reduction is very slow. Cyclic anhydrides slowly consume 2 equiv of hydride, corresponding to reduction to the caboxylic acid and alcohol stages. Acid chlorides, esters, and lactones are rapidly and quantitatively reduced to the corresponding carbinols. Epoxides consume 1 equiv hydride slowly. Primary amides evolve 1 equiv of hydrogen readily, but further reduction is slow. Tertiary amides are also reduced slowly. Both aliphatic and aromatic nitriles consume 1 equiv of hydride rapidly, but further hydride uptake is slow. Analysis of the reaction mixture with 2,4-dinitrophenylhydrazine yields 64% of caproaldehyde and 87% of benzaldehyde, respectively. 1-Nitropropane utilizes 2 equiv of hydride, one for hydrogen evolution and the other for reduction. Other nitrogen compounds examined are also reduced slowly. Cyclohexanone oxime undergoes slow reduction to N-cyclohexylhydroxyamine. Pyridine ring is slowly attacked. Disulfides examined are reduced readily to the correponding thiols with rapid evolution of 1 equiv hydrogen. Dimethyl sulfoxide is reduced slowly to dimethyl sulfide, whereas the reduction of diphenyl sulfone is very slow. Sulfonic acids only liberate hydrogen quantitatively without any reduction. Finally, cyclohexyl tosylate is inert to this reagent. Consequently, potassium 2-thexyl-1,3,2-dioxaborinane hydride, a monoalkyldialkoxyborohydride, shows a unique reducing characteristics. The reducing power of this reagent exists somewhere between trialkylborohydrides and trialkoxyborohydride. Therefore, the reagent should find a useful application in organic synthesis, especially in the field of selective reduction.

• Journal of Microbiology and Biotechnology
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• v.25 no.5
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• pp.704-708
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• 2015

For the analysis of multiple-reaction intermediates for long-chain dicarboxylic acid biotransformation, simple and reproducible methods of extraction and derivatization were developed on the basis of gas chromatography with flame ionization detector (GC-FID) instead of mass spectrometry. In the derivatization step, change of the ratio of pyridine to MSTFA from 1:3 to 9:1 resulted in higher peak intensity (p = 0.021) and reproducibility (0.6%CV) when analyzing 32 g/l ricinoleic acid (RA). Extraction of RA and ω-hydroxyundec-9-enoic acid with water containing 100 mM Tween 80 showed 90.4-99.9% relative extraction efficiency and 2-7%CV compared with those with hydrophobic ethyl acetate. In conclusion, reduction of the pyridine content and change of the extraction solvent to water with Tween 80 provided compatible derivatization and extraction methods to GC-FID-based analysis of longchain carboxylic acids.

• Bulletin of the Korean Chemical Society
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• v.5 no.6
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• pp.240-244
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• 1984

8-Oxyquinoline dihydroboronite is prepared by mixing equimolar amounts of 8-hydroxyquinoline and borane-dimethyl sulfide complex in tetrahydrofuran at room temperature and its structure is determined by spectroscopic methods. The reagent is shown to be an extremely mild reducing agent and reduces aldehydes, cyclohexanones, and acid chlorides to some extent. The reagent in the presence of 0.1 equiv of boron trifluoride etherate in tetrahydrofuran at room temperature reduces selectively aldehydes in the presence of ketones, while the reagent in the presence of 1 equiv of boron trifluoride etherate rapidly reduces simple aldehydes and ketones but does not reduce carboxylic acids, esters, and amides.

• Bulletin of the Korean Chemical Society
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• v.8 no.4
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• pp.285-291
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• 1987

The approximate rates, stoichiometries and products of the reaction of potassium triethylborohydride $(KEt_3BH)$ with selected organic compounds containing representative functional groups under the standard condition $(0^{\circ}C,$ THF) were examined in order to explore the reducing characteristics of this reagent as a selective reducing agent. Primary alcohols, phenols and thiols evolve hydrogen rapidly whereas secondary and tertiary alcohols evolve very slowly. n-Hexylamine is inert to this reagent. Aldehydes and ketones are reduced rapidly and quantitatively to the corresponding alcohols. Reduction of noncamphor gives 3% exo- and 97% endo-norboneol. Anthraquinone is cleanly reduced to 9,10-dihydro-9,10-dihydroxyanthracene stage. Carboxylic acids liberate hydrogen rapidly and quantitatively but further reduction does not occur. Anhydrides utilize 2 equiv of hydride to give an equimolar mixture of acid and alcohol. Acid chlorides, esters and lactones are rapidly and quantitatively reduced to the corresponding alcohols. Epoxides are reduced at moderate rates with Markovnikov ring opening to give the more substituted alcohols. Primary amides liberate 1 equiv of hydrogen rapidly. Further reduction of caproamide is slow whereas benzamide is not reduced. Tertiary amides are reduced slowly. Benzonitrile utilizes 2 equiv of hydride in 3 h to go to the amine stage whereas capronitrile takes only 1 equiv. The reaction of nitro compounds undergo rapidly whereas azobenzene and azoxybenzene are reduced slowly. Cyclohexanone oxime rapidly evolves hydrogen without reduction. Phenyl isocyanate utilizes 1 equiv of hydride to proceed to formanilide stage. Pyridine N-oxide and pyridine is reduced rapidly. Disulfides are rapidly reduced to the thiol stage whereas sulfoxide, sulfonic acid are practically inert to this reagent. Sulfones and cyclohexyl tosylate are slowly reduced. Octyl bromide is reduced rapidly but octyl chloride and cyclohexyl bromide are reduced slowly.

• Bulletin of the Korean Chemical Society
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• v.15 no.2
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• pp.132-138
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• 1994

Bis(diethylamino)aluminum hydride was utilized in a systematic study of the approximate rates and stoichiometry of the reaction of excess reagent with 55 selected organic compounds containing representative functional groups under standardized conditions (THF, $0^{\circ}C$, reagent to compound=4 : 1) in order to define the characteristics of the reagent for selective reductions. The reducing action of BEAH was also compared with that of the parent aluminum hydride. The reducing action of the reagent is quite similar to that of aluminum hydride, but the reducing power is much weaker. Aldehydes and ketones were readily reduced in 1-3 h to the corresponding alcohols. However, unexpectedly, a ready involvement of the double bond in cinnamaldehyde was realized to afford hydrocinnamyl alcohol. The introduction of diethylamino group to the parent aluminum hydride appears not to be appreciably influential in stereoselectivity on the reduction of cyclic ketones. Both p-benzoquinone and anthraquinone utilized 2 equiv of hydride readily without evolution of hydrogen, proceeded cleanly to the 1,4-reduction products. Carboxylic acids and acid chlorides underwent reduction to alcohols slowly, whereas cyclic anhydrides utilized only 2 equiv of hydride slowly to the corresponding hydroxylacids. Especially, benzoic acid with a limiting amount of hydride was reduced to benzaldehyde in a yield of 80%. Esters and lactones were also readily reduced to alcohols. Epoxides examined all reacted slowly to give the ring-opened products. Primary and tertiary amides utilized 1 equiv of hydride fast and further hydride utilization was quite slow. The examination for possibility of achieving a partial reduction to aldehydes was also performed. Among them, benzamide and N,N-dimethylbenzamide gave ca, 90% yields of benzaldehyde. Both the nitriles examined were also slowly reduced to the amines. Unexpectedly, both aliphatic and aromatic nitro compounds proved to be relatively reactive to the reagent. On the other hand, azo- and azoxybenzenes were quite inert to BEAH. Cyclohexanone oxime liberated 1 equiv of hydrogen and utilized 1 equiv of hydride for reduction, corresponding to N-hydroxycyclohexylamine. Pyridine ring compounds were also slowly attacked. Disulfides were readily reduced with hydrogen evolution to the thiols, and dimethyl sulfoxide and diphenyl sulfone were also rapidly reduced to the sulfides.