• Title/Summary/Keyword: ${\alpha},{\beta}$-unsaturated compounds

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Reductive Amination of ${\alpha}$,${\beta}$-Unsaturated Carbonyl Compounds with Tetracarbonylhydridoferrate as a Reducing Agent (${\alpha}$,${\beta}$-不飽和 카르보닐化合物의 還元 아미노화反應)

  • Kim Hong-Seok;Shim Sang Chul;Shim Sang Chull
    • Journal of the Korean Chemical Society
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    • v.23 no.2
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    • pp.99-103
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    • 1979

  • The reductive amination of three ${\alpha}$,${\beta}$-unsaturated aldehydes, cinnamaldehyde, crotonaldehyde, and acrolein are carried out successfully by tetracarbonylhydridoferrate in the presence of various primary amines. In a typical reaction, a mixture of potassium tetracarbonylhydridoferrate (22 mmole), an amine (22∼44 mole) and ${\alpha}$,${\beta}$-unsaturated aldehyde (22 mmole), in ethanol (30∼50 ml) was stirred for 9∼60 hours at room temperature under carbon monoxide atmosphere. All the products were characterized as secondary amines by mass, infrared, and nmr spectra as well as gas chromatographic data.

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Highly Chemo- and Regioselective Reaction of Hydroxybenzenes in Acidic Ionic Liquid

  • Guo, Hui;Zhuang, Yu Wei;Cao, Jian;Zhang, Guo Bao
    • Bulletin of the Korean Chemical Society
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    • v.34 no.9
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    • pp.2594-2596
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    • 2013

  • Highly chemo- and regioselective reaction of hydroxybenzenes with ${\alpha},{\beta}$-unsaturated compounds in acidic ionic liquid l-butyl-3-methylimidazolium hydrogen sulphate ([BMIM]HSO4) was reported for the first time. A series of oxa-Michael adducts and Friedel-Crafts alkylated products were synthesized with good yields. The acidic ionic liquid could be easily recycled for at least 5 times with only minor loss in activity.

  • https://doi.org/10.5012/bkcs.2013.34.9.2594 인용 PDF KSCI

Selective Reduction by Lithium Bis-or Tris(dialkylamino)-aluminum Hydrides. II. Reaction of Lithium Tris(dibutylamino)-aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Cha, Jin-Soon;Lee, Sung-Eun;Lee, Heung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.12 no.6
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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.

  • https://doi.org/10.5012/bkcs.1991.12.6.644 인용 PDF

Selective Epoxidation and Reduction of Rigid Cyclic ${\alpha},{\beta}$-Unsaturated Carbonyl Compounds (환상 ${\alpha},{\beta}$-불포화 카르보닐 화합물의 선택적 에폭시화 및 환원)

  • Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.49 no.6
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    • pp.443-448
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    • 2005

  • Diosgenin (25 (R) - spirost-5-en-3$\beta$ -ol) was oxidized with 2,3-dichloro -5,6-dicyano-1,4-benzoquinone to form 25(R)-1,4,6-spirostatrien-3-one (1) as rigid cyclic $\alpha$,$\beta$-unsaturated carbonyl compound. This compound was reacted with $H_{2}O_{2}$, m-chloroperoxybenzoic acid (mCPBA), NaOCl in the presence with (R,R)- or (S,S)-Jacobsen catalyst, tert-butyl-hydroperoxide (TBHP) in Mo$(CO)_{6}$, and in VO $(acac)_{2}$ catalyst, respectively, 25(R) -1,4,6-spirostatrien -3-one (1) was reduced with $NaBH_{4}$ L-Selectride, $LiAIH_{4}$,$BH_{3}$ $\cdot$$(CH_{3})_{2}S$, Superhydride, Red-Al, and lithium tri-tert-butoxyaluminium hydride. And 25(R)-4,6-spirostadien-3$\beta$-ol (4) was treated with $H_{2}O_{2}$, mCPBA, TBHP in D - (-) - and L-(+)-diisopropyltar-trate and $Ti(OiPr)_{4}$ condition (Sharpless asymmetric epoxidation), TBHP in $Mo(CO)_{6}$, and in $VO(acac)_{2}$ catalyst, respectively.

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