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환원시약인 테트라카르보닐철산염(O)을 이용한 유기아지드화물의 아미노화(제1보)
沈相喆,崔貴南 慶北大學校 物理化學硏究所 1985 硏究論文集 Vol.6 No.-
유기아지드화물은 일산화탄소대기압하, 실온에서 높은 선택적 환원시약인 테트라카르 보닐철산염의 존재하에서 높은 수득율의 아민으로 환원되었다. 특히 벤조일아지드는 동일시약내 일산화탄소 대기압 실온에서는 에틸페닐카바메이트를 주나, -40℃에서는 정량적으로 벤즈아미드가 얻어졌다. Organic azides were reduced to organic amines in the presence of tetracarbonylhydridoferrate(O) as a highly selective reducing agent at room temperature under carbon monoxide atmosphere. Particularly, benzoylazide gave ethylphenylcarbamate at room temperature but gave benzamide quantitatively at -40℃ in the presence of tetracarbonylhydridoferrate under carbon monoxide atmosphere.
사 카르보닐 철산염을 촉매로한 말론 혹은 숙신 디클로리드와 알코올로 부터 디에스테르의 편리한 합성
沈相喆,許根泰,李學沂,吳淳世,徐恩德 경북대학교 1987 論文集 Vol.43 No.-
A large variety of alcohols react with diacid dichlorides such as malonic and succinic dichloride in the presence of a catalytic amount of tetracarbonylhydridoferrate at room temperature under carbon monoxide or nitrogen to give the corresponding diesters in good yields. It is also worthy of note that diethyl malonate is obtained in 97% yield using KHFe(O)_4 as a catalyst and in only 38% yield when K_2Fe(CO)_4 is used. The addition of acid-trapping agents such as triethylamine or N, N-dimethylaniline is not necessary. The mechanism of these reactions is investigated.
전이금속촉매-일산화탄소-물계에 의한 카르보닐 화합물의 히드로히드록시 메틸화 반응
심상철,민경은,허근태 慶北大學校 1983 論文集 Vol.36 No.-
Dialdehydes such as adipaldehyde, glutaraldehyde and succinaldehyde were reduced to give their corresponding 1,6-hexanediol, 1,5-pentanediol and 1,4-butanediol in good yields in the presence of catalytic amounts hexarhodium hexadecacarbonyl or iron pentacarbonyl in water and methoxyethanol or ethanol at 180℃ for 4hr under pressures of carbon monoxide. Under the same conditions, diketones such as 2,5-hexanedione, 2,4-pentanedione and 2,3-butanedione were afforded their corresponding 2,5-hexanediol, 2,4-pentanediol and 2,3-butanediol in moderate yields. Glyoxal also gave ethyleneglycol. Paraformaldehyde with formaldehyde can be converted into ethyleneglycol by this procedure. 4-Oxopentanal, hydroormylation of methyl-vinylketone was obtained 1,4-pentanediol in poor yield. With hydrohydroxymethylation of dialdehydes, rhodium or iron carbonyl complexes as catalyst precursors, Rh_6(CO)_16 and Fe(CO)_5, are more effective than (RhCl(NBD))_2, RhH(CO)(PPh_3)_3 and KHFe(CO)_4. 1,5-Pentanediol and 1,4-butanediol are obtainable in more than 80% yields by using Rh_6(C)_16 and Fe(CO)_5, while (RhCl(NBD))_2 and RhH(C))(PPh_3)_3 give the product in less than 45% yields. These results indicate that carbon monoxide enhances the catalytic activity of the rhodium or iron by coordination. Accordingly, the reaction seems to proceed via water gas shift reaction(CO+H_2O=H_2+CO_2). The fact that dialdehydes of diketones were readily hydrogenated to give diols, suggests that these reactions appeared to include a nucleophilic attack of water on a metal coordinated carbonyl to give a metal hydride intermediate which is active for the hydrogenation. The present results have provided a novel method(for hydroxymethylation of di-carbonyl) catlyzed by transition metal complexes in the presence of water under pressures of carbon monoxide.
沈相喆,白振旭 경북대학교 산업기술연구소 1988 産業技術硏究誌 Vol.16 No.-
The reaction of 2-methyl-3-butyn-2-ol with secondary amine in the presence of a catalytic amount of lanthanide chloride in acetonitrile at 160℃ for 8 hr gave the corresponding 1, 1-dimethyl-2-oxopropyl N, N-dialkylcarbamate in reasonable yield with a small amount of N, N-dialkylacetamide under 20 atm of carbon dioxide. The yield of 1, 1-dimethyl-2-oxopropyl N, N-dialkyl carbamates depends of the catalyst. In the case of 1, 1-dimethyl-2-oxopropyl N, N-hexa-methylene carbamate, CeCl_3 gave 38% yield, but NdCl_3, CdCl_3, and PrCl_3 gave 20%, 22% and 27% yield, respectively.
沈相喆,許根泰 경북대학교 교육대학원 1982 논문집 Vol.14 No.-
The reaction of 2,5-hexanedione or succinaldehyde to be hydrolyzed 2,5-dimethoxytetrahydrofuran by acid with a variety of aryl-and alkylamines using tetracarbonylhydridoferrate as a highly selective reducing agent at room temperature or 60℃ under an atmosphere of carbon monoxide gave the corresponding N-substituted 2,5-dimethylpyrrolidines or N-substituted pyrrolidines in good to excellent yields. The reduction of synthesized 5-nitro-2-hexanone with benzaldehyde in this reagent was also obtained N-benzyl-2,5-dimethyl pyrrolidine in good yield. And aniline reacts with propanal having two α-hydrogens in the presence of a catalytic amount of a rhodium complex in neutral medium at 180℃ to give quinoline and tetrahydroquinoline derivatives in moderate yield. The mechanism of these reactions was investigated.
轉移金屬錯物 觸媒에 의한 벤잘할라이드류의 카르보닐화에 關한 硏究
沈相喆,都七焄,李東燁,尹永炷 경북대학교 교육대학원 1991 논문집 Vol.23 No.-
벤잘브로미드, 알코올, KHCO_3 및 촉매로써 Co_2(Co)_8을 상압하 실온에서 반응시켜 알킬 페닐아세테이트와 중간체로써 알킬 α-브로모페닐아세테이트를 각각 보통 수들율로 주었다. 이 반응세어의 염기는 산포착제로써 또는 촉매촉진제의 두가지 목적으로 사용되었다. Treatment of benzal bromide, alcohol, potassium bicarbonate, and cobalt octacarbonyl as a catalyst at room temperature under one atmospheric pressure of carbon monoxide gave alkylphenylacetate and alkyl α-bromophemylacetate as an intermediate in moderate yields, respectively. The base in this reaction is used not only as an acid scanvenger but also as a catalyst activator.
철카보닐음이온과 카복실산무수물 및 카복실산탄산무수물의 반응
심상철,이학기,홍영석 경북대학교 교육대학원 1977 논문집 Vol.8 No.-
Disodium tertacarbonylferrate reacts readily aliphatic, aromatic carboxylic anhydrides. The corresponding aldehydes are formed in high yields by quenching the reaction solution with acetic acid. The reaction mechanism via acylcarbonylferrate is assumed.
선택적 환원시약인 사카르보닐 철산염(O)을 이용한 N-치환-2,5-디메틸 피로리딘 유도체의 용이한 합성
심상철,허근태,김기두,김우식,Sang Chul Shim,Keun Tai Huh,Kee Doo Kim,Woo Sik Kim 대한화학회 1986 대한화학회지 Vol.30 No.4
선택적 환원시약인 사카르보닐 철산염(O)을 상압의 일산화탄소하 실온 및 60${\circ}C$에서 2,5헥산디온과 각종 일차아민과 반응시켜 대응하는 N-치환 2,5-디메틸 피로리딘 유도체를 좋은 수득율로 얻을 수 있었다. 또한 미리 합성된 5-nitro-2-hexanone과 벤즈알데히드는 사카르보닐 철산염의 존재하, 상압의 일산화탄소, 150${\circ}C$의 고압솥반응에서 N-qoswkf-2,5-디메틸 피로디딘이 보통 수득율로 얻어졌다. 이들 반응의 메카니즘도 검토 하였다. The reaction of 2,5-hexanedione with a variety of primary amines using tetracarbonylhydridoferrate(O) as a selective reducing agent at room temperature or 60${\circ}C$ under an atmosphere of carbon monoxide gave the corresponding N-substituted 2,5-dimethylpyrrolidine derivatives. The reaction of synthesized 5-nitro-2-hexanone with benzaldehyde in the presence of tetracarbonylhydridoferrate(O) at 150${\circ}C$ under an atmosphere of carbon monoxide in an autoclave also gave N-benzyl-2,5-dimethylpyrrolidine in moderate yield. The mechanism of these reactions was investigated.
사카르보닐 철산염, HFe(CO)$_4^-$을 이용한 숙신알데히드와 페닐렌디아민으로부터 피로리디노벤젠의 편리한 합성
심상철,우병원,도칠훈,최귀남,여영국,Sim, Sang Cheol,U, Byeong Won,Do, Chil Hun,Choe, Gwi Nam,Yeo, Yeong Guk 대한화학회 1990 대한화학회지 Vol.34 No.6
에탄올성 사카르보닐 철산염, HFe(CO)$_4^-$와 수용성 숙신알데히드를 조합하면 아미노기를 피롤리딘 고리로 선택적 전환을 하는데 매우 효과적이다. 페닐렌디아민은 일산화탄소 압력, 실온, 철산염존재하에서 숙신알데히드와 반응해서 대응하는 피롤리딘을 보통의 수득률로 주었다. 이 반응에 철산염-숙신알데히드-페닐렌디아민계에서 몰비가 1.0:1.0:1.0일 때는 1개의 피롤리딘고리를, 1.0:2.0:1.0의 경우는 두개의 피롤리딘 고리를 선택적으로 주었다. Ethanolic tetracarbonylhydridoferrate, HFe(CO)$_4^-$, combined with aqueous succinaldehyde is very efficient for the selective transformation of an amino group into a pyrrolidine ring. Phenylendiamines react with aqueous succinaldehyde in the presence of HFe(CO)$_4^-$, at room temperature under atmospheric pressure of carbon monoxide to give the corresponding pyrrolidines in moderate yields. In these reactions, the molar ratio of 1.0:1.0:1.0 of the ferrate-succinaldehydephenylenediamine system gave one pyrrolidine ring, and the case of 1.0:2.0:1.0 gave two pyrrolidine rings, selectively.