• Title/Summary/Keyword: aldehydes

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One-pot Four Component Reaction of Unsymmetrical 1-Methylbarbituric Acid with BrCN and Various Aldehydes in the Presence of Et3N and/or Pyridine

  • Jalilzadeh, Mohammad;Pesyan, Nader Noroozi
    • Journal of the Korean Chemical Society
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    • v.55 no.6
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    • pp.940-951
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    • 2011
  • Reaction of 1-methylpyrimidine-(1H,3H,5H)-2,4,6-trione (1-MBA 1) as an unsymmetrical barbituric acid with cyanogen bromide and various aldehydes in the presence of triethylamine and/or pyridine afforded diastereomeric mixtures of new class of heterocyclic stable 5-aryl-1,1'-dimethyl- and 5-aryl-3,1'-dimethyl-1H,1'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]2,2',4,4',6'(3H,3'H,5H)-pentaones which are dimeric forms of 1-methyl barbiturate at the range of $0^{\circ}C$ to room temperature. In the reaction of some aldehydes with 1-MBA and BrCN were afforded a mixture of diastereomers. Another two aldehydes such as 4-cyano- and 2-hydroxybenzaldehydes gave exclusively two diastereomers in which binded to the salt of triethylammonium hydrobromide by intermolecular H-bond in ratio of 1:1. 4-Hydroxybenzaldehyde and 2-pyridinecarbaldehyde gave exclusively one diastereomer under the same condition. Aldehydes possessing strong electron-donor were produced exclusively two geometric isomers of Knoevenagel adduct (E- and Z-isomers). The structures of compounds were deduced by $^1H$ NMR, $^{13}C$ NMR and FT-IR spectroscopy. Mechanism of the formation is discussed.

Prediction of Explosion Limits of Aldehydes Using Chemical Stoichiometric Coefficients and Heats of Combustion (연소열 및 화학양론계수를 이용한 알데히드류의 폭발한계의 예측)

  • Ha, Dong-Myeong
    • Journal of the Korean Institute of Gas
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    • v.19 no.2
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    • pp.5-11
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    • 2015
  • The explosion limit is one of the major combustion properties used to determine the fire and explosion hazards of the flammable substances. The explosion limit of aldehydes have been shown to be correlated the heat of combustion and the chemical stoichiometric coefficients. In this study, the lower explosion and upper explosion limits of aldehydes were predicted by using the heat of combustion and chemical stoichiometric coefficients. The values calculated by the proposed equations agreed with literature data above determination coefficient 0.99. From the given results, using the proposed methodology, it is possible to predict the explosion limits of the aldehydes.

Direct Organocatalytic Regioselective α-Hydroxyamination of α-Branched Aldehydes

  • Kim, Sung-Gon;Ahn, Eun-Ju;Park, Tae-Ho
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1665-1669
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    • 2007
  • A direct regioselective α-hydroxyamination of α-branched aldehydes with nitrosobenzene using cis-5-benzylproline as catalyst has been developed for the preparation of α-hydroxyamino aldehydes possessing a quaternary carbon center. Such compounds are versatile building blocks for the synthesis of quaternary α- amino acids, β-amino alcohols, and 1,2-diamines.

Solvent-free Synthesis of Propargylic Alcohols using ZnO as a New and Reusable Catalyst by Direct Addition of Alkynes to Aldehydes

  • Hosseini-Sarvari, Mona;Mardaneh, Zahra
    • Bulletin of the Korean Chemical Society
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    • v.32 no.12
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    • pp.4297-4303
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    • 2011
  • Under solvent-free conditions, the synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes promoted by ZnO as a novel, commercially, and cheap catalyst is described. Furthermore, the catalyst can be reused for several times without any significant loss of its catalytic activity.

Two Phase Oxidation of Aldehydes with Chromic Acid

  • Jae Soon Kim;Tae Soung Huh;Nung Min Yoon
    • Journal of the Korean Chemical Society
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    • v.15 no.2
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    • pp.65-68
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    • 1971
  • The possibility of the two-phase oxidation of an aldehyde to carboxylic acid was studied. Thus the ether solutions of representative aldehydes (2.0M) were treated with 1.5 mole equivalent of chromic acid solution (1.0M) for 30 minutes at room temperature. Of the ten aldehydes tested,m butanal, benzaldehyde, tolualdehyde, o-, m-, p-nitrobenzaldehyde and cinnamaldehyde could be oxidized conveniently to the corresponding carboxylic acid giving an 80-90% yield. But furfural gave only a 30% yield of furoic acid and the oxidation of salicylaldehyde was unsuccessful.

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Phosphomolybdic Acid Supported on Silica Gel as an Efficient and Reusable Catalyst for Cyanosilylation of Aldehydes

  • Kadam, Santosh T.;Kim, Sung-Soo
    • Bulletin of the Korean Chemical Society
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    • v.29 no.7
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    • pp.1320-1322
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    • 2008
  • Phosphomolybdic acid supported on silica gel (PMA-$SiO_2$) is an efficient catalyst for the activation of TMSCN for the facile cyanosilylation of various aldehydes. Cyano transfer from TMSCN to aldehyde proceeds smoothly at rt in presence of 0.8 mol % of PMA-$SiO_2$ leading to a range of cyanosilylether in excellent yield (mostly over 93%) within short reaction time (30 min). The catalyst can be recovered and reused several times without loss of activity.

Concomitant Addition and Acetalization of α,β-Unsaturated Aldehydes with Diols

  • Jeon, Kyu-Ok;Yu, Ji-Sook;Lee, Chang-Kiu
    • Bulletin of the Korean Chemical Society
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    • v.25 no.11
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    • pp.1653-1656
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    • 2004
  • ${\alpha},{\beta}$-Unsaturated aldehydes such as acrolein and crotonaldehyde were reacted with diols in the presence of conc. sulfuric acid to give products of which concomitant addition to C-C double bond and acetalization took place. Boron trifluoride etherate and titanium tetrachloride gave only acetalization products.

Selective Reduction of Carbonyl Compounds with B-Alkoxydiisopinocampheylborane

  • 차진순;권오운;김종미
    • Bulletin of the Korean Chemical Society
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    • v.17 no.8
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    • pp.725-729
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    • 1996
  • Reaction of carbonyl compounds with B-alkoxydiisopinocampheylborane (Ipc2BOR, R=H, Et, i-Pr, t-Bu) was investigated in detail in order to establish their usefulness as selective reducing agents. The reagents were extremely mild and reduced only aldehydes effectively under mild conditions. The reagents also reduced α,β-unsaturated aldehydes to the corresponding allylic alcohols without any detectable 1,4-reduction. Furthermore, aldehydes can be reduced in the presence of epoxides and acid chlorides. Consequently, the selective reduction of aldehyde groups in the presence of keto and all other functional groups has been realized with these reagents.

Partial Reduction of Nitriles to Aldehydes by Thexylbromoborane-Methyl Sulfide$^\dag$

  • Cha, Jin-Soon;Oh, Se-Yeon;Kim, Jin-Euog
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.301-304
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    • 1987
  • A systematic study of the partial reduction of nitriles to the corresponding aldehydes with thexylbromoborane-methyl sulfide $(ThxBHBr{\cdot}SMe_2)$ under practical conditions has been carried out. The yields of aldehydes are good in the aliphatic series. However, the yields of aromatic series vary with substituents and ring itself.

Reduction of Selected Carbonyl Compounds with 8-Oxyquinoline Dihydroboronite. Selective Reduction of Aldehydes in the Presence of Ketones

  • Kim, Sung-Gak;Yang, Sung-Bong;Kang, Ho-Jung
    • 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.