2396-43-2Relevant academic research and scientific papers
Determination of ceiling temperature and thermodynamic properties of low ceiling temperature polyaldehydes
Schwartz, Jared M.,Engler, Anthony,Phillips, Oluwadamilola,Lee, Jihyun,Kohl, Paul A.
, p. 221 - 228 (2018)
Knowledge of the ceiling temperature and thermodynamic variables for low ceiling temperature polymers is critical to understanding the material's synthesis and use. Synthesis of the polymer below its ceiling temperature is the routine polymerization route. In situ 1H NMR of the equilibrium polymerization reaction can provide critical information for determining the enthalpy and entropy of polymer formation. Three polyaldehydes were synthesized with in situ 1H NMR, and their energies of formation were determined for the linear region of ceiling temperature. Insights into the mechanism of polymerization were also found using this method.
Novel acidic ionic liquids as efficient and recyclable catalysts for the cyclotrimerization of aldehydes
Song, Heyuan,Chen, Jing,Xia, Chungu,Li, Zhen
, p. 266 - 273 (2012)
A mild, efficient, and ecofriendly procedure for cyclotrimerization of aldehydes was realized by using a series of novel Brnsted acidic ionic liquids (BAILs) consisting of double-SO3H groups in cations as catalysts. Good conversion of aldehydes and selectivity of trialkyl-1,3,5-trioxanes were achieved by using 1mol% of BAILs. In addition, the catalyst system could be recycled and reused at least eight times without apparent loss of activity. Taylor & Francis Group, LLC.
Synthesis of 1,3,5-trioxanes: A new, simple method using a bentonitic earth as catalyst
Camarena,Cano,Delgado,Zuniga,Alvarez,Garcia
, p. 6857 - 6858 (1993)
A simple method for synthesizing aliphatic as well as aromatic 1,3,5-trioxanes using as catalyst a bentonitic earth is reported. The yields ranged from good to excellent.
A convenient approach for the synthesis of 1,3,5-trioxanes under solvent-free conditions at room temperature
Li, Xinzhong,Lin, Qi,Cao, Rong
, p. 1017 - 1022 (2014)
A series of environmentally benign bis-SO3H-functionalized Bronsted acidic ionic liquids were synthesized by using aliphatic polyamines and 1,3-propanesultone as the source chemicals. These ionic liquids acted as efficient inexpensive and recyclable catalysts for cyclotrimerization of aliphatic aldehydes at room temperature under solvent-free conditions. The reactions proceeded smoothly with good to excellent isolated yields (66.9-97.6 %=) and were generally complete in 1.5 h when the amount of ionic liquids was 0.1 mol%. The ionic liquids could be recovered readily and reused five times without any significant loss in their catalytic activity. Graphical abstract: [Figure not available: see fulltext.]
Antimony(v) cations for the selective catalytic transformation of aldehydes into symmetric ethers, α,β-unsaturated aldehydes, and 1,3,5-trioxanes
Arias Ugarte, Renzo,Devarajan, Deepa,Mushinski, Ryan M.,Hudnall, Todd W.
supporting information, p. 11150 - 11161 (2016/07/20)
1-Diphenylphosphinonaphthyl-8-triphenylstibonium triflate ([2][OTf]) was prepared in excellent yield by treating 1-lithio-8-diphenylphosphinonaphthalene with dibromotriphenylstiborane followed by halide abstraction with AgOTf. This antimony(v) cation was found to be stable toward oxygen and water, and exhibited exceptional Lewis acidity. The Lewis acidity of [2][OTf] was exploited in the catalytic reductive coupling of a variety of aldehydes into symmetric ethers of type L in good to excellent yields under mild conditions using Et3SiH as the reductant. Additionally, [2][OTf] was found to selectively catalyze the Aldol condensation reaction to afford α-β unsaturated aldehydes (M) when aldehydes with 2 α-hydrogen atoms were used. Finally, [2][OTf] catalyzed the cyclotrimerization of aliphatic and aromatic aldehydes to afford the industrially-useful 1,3,5 trioxanes (N) in good yields, and with great selectivity. This phosphine-stibonium motif represents one of the first catalytic systems of its kind that is able to catalyze these reactions with aldehydes in a controlled, efficient manner. The mechanism of these processes has been explored both experimentally and theoretically. In all cases the Lewis acidic nature of the antimony(v) cation was found to promote these reactions.
Montmorillonite clay-catalyzed hetero-Diels-Alder reaction of 2,3-dimethyl-1,3-butadiene with benzaldehydes
Dintzner, Matthew R.,Little, Andrew J.,Pacilli, Massimo,Pileggi, Dominic J.,Osner, Zachary R.,Lyons, Thomas W.
, p. 1577 - 1579 (2008/02/03)
Montmorillonite K10 clay was found to catalyze the hetero-Diels-Alder reaction of 2,3-dimethyl-1,3-butadiene with o-anisaldehyde and other benzaldehyde derivatives; a transition state involving chelation of the clay's metal ions with the dienophile's heteroatoms is proposed.
InCl3 as an efficient catalyst for cyclotrimerization of aldehydes: Synthesis of 1,3,5-Trioxane under solvent-free conditions
Elamparuthi,Ramesh,Raghunathan
, p. 2801 - 2804 (2007/10/03)
1,3,5-Trioxanes derived from aldehydes were synthesized using indium trichloride as a catalyst. Cyclotrimerization of the aldehydes gave excellent yields under neat conditions within a short span of time. Copyright Taylor & Francis, Inc.
Tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization catalyzed by an organotungsten Lewis acid
Wang, Hsing-Shiun,Yu, Shuchun Joyce
, p. 1051 - 1055 (2007/10/03)
The tris(2-pyridyl)phosphine complex [P(2-py)3 W(CO)(NO)2](BF4)2 acts as a Lewis acid catalyst precursor for the tandem reactions of Friedel-Crafts/aldehyde cyclotrimerization, which lead to the formation of a series of hyper-branched star polymers.
TaCl5-Silicagel and TaCl5 as new Lewis acid systems for selective tetrahydropyranylation of alcohols and thioacetalisation, trimerisation and aldolisation of aldehydes
Chandrasekhar,Takhi, Mohamed,Reddy, Y. Ravindra,Mohapatra, Suchismita,Rao, C. Rama,Reddy, K. Venkatram
, p. 14997 - 15004 (2007/10/03)
TaCl5 adsorbed on silicagel has been utilized for the first time as Lewis acid catalyst for protection of aldehydes and alcohols as thiocetals and THP ethers respectively. Similarly TaCl5 has been exploited as an useful Lewis acid for chemoselective trimerisation and/or aldolisation of aldehydes.
BiCl3-catalyzed Mukaiyama-aldol and carbonyl-ene reactions
Peidro, Laurence,Le Roux, Christophe,Laporterie, Andre,Dubac, Jacques
, p. 397 - 399 (2007/10/03)
The H-ene pathway has not been detected for the bismuth(III) chloride-catalyzed Mukaiyama-aldol reaction involving silyl enol ethers and aldehydes. The silatropic ene-like process is the only mechanism observed, even with the weakly reactive 1-(trimethylsilyloxy) cyclohexene. However, trimerization of an aliphatic aldehyde can occur.
