6465-95-8

Usage

InChI:InChI=1/C9H12O/c1-6-7-2-3-8(4-7)9(6)5-10/h2-3,5-9H,4H2,1H3

Upstream product

• 542-92-7 cyclopenta-1,3-diene 
• 123-73-9 crotonaldehyde 
• 123-73-9 trans-Crotonaldehyde 
• 77-73-6 bi(cyclopentadiene) 

Downstream Products

• 6268-90-2 4-(3-methyl-norborn-5-en-2-yl)-but-3-en-2-one 
• 6968-75-8 2-hydroxymethyl-3-methyl-bicyclo[2.2.1]heptane 
• 4397-23-3 (3-endo,2-exo)-3-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid 
• 4397-23-3 endo-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid 

Relevant academic research and scientific papers

Transition metal catalysis of the Diels-Alder reaction

Catalysis of the Diels-Alder reaction by the transition metal Lewis acid, (n5-C5H5)Fe+(CO)[P(OCH3)3](THF)BF4-, is reported.

Investigations into the use of niobium and tantalum complexes as Lewis acids

The Lewis acidity of niobium and tantalum compounds has been studied with respect to simple Diels-Alder reactions. The results show that these compounds have excellent Lewis acidity.

Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis

Lewis acids are frequently employed in catalysis but they often suffer from high moisture sensitivity. In many reactions, catalysts are deactivated because of the problem that strong Lewis acids also bond to the products. In this research, hydrolytically stable bidentate Lewis acid catalysts derived from selenonium dicationic centers have been developed. The bis-selenonium catalysts are employed in the activation of imine and carbonyl groups in various transformations with good yields and selectivity. Lewis acidity of the bis-selenonium salts was found to be stronger than that of the monoselenonium systems, attributed to the synergistic effect of the two cationic selenonium centers. In addition, the bis-selenonium catalysts are not inhibited by strong bases or moisture.

Chiral Imidazolidin-4-one with catalytic amount of Dicationic ionic liquid act as a recoverable and reusable Organocatalyst for asymmetric Diels-Alder reaction

Imidazolidin-4-one is used as a recoverable organocatalyst for the asymmetric Diels-Alder reaction in the presence of catalytic amount of dicationic ionic liquid and trifluoroacetic acid as a co-catalyst. The Diels-Alder reaction between model substrate cyclopentadiene and crotonaldehyde gave the product in 95% conversion and 87% ee of the endo-product. The catalyst was shown better reusability when the 20?mol% of dicationic ionic liquid was used and catalyst was reused upto 5 cycles, conversion remains upto 3 recycles but ee of endo-9 was slightly droped.

Arene-Ruthenium Complexes of 1,1′-Bis(ortho-carborane): Synthesis, Characterization, and Catalysis

Deprotonation of 1,1′-bis(ortho-carborane) with nBuLi in THF followed by reaction with [RuCl2(p-cymene)]2 affords, in addition to the known compound [Ru(κ3-2,2′,3′-{1-(1′-closo-1′,2′-C2B10H10)-closo-1,2-C2B10H10)}(p-cymene)] (I), a small amount of a new species, [Ru(κ3-2,2′,11′-{1-(7′-nido-7′,8′-C2B9H11)-closo-1,2-C2B10H10)}(p-cymene)] (1a), with two B-agostic B-H?Ru bonds, making the bis(carborane) unit a closo-nido-X(C)L2 ligand, a previously unreported bonding mode. Similar species were also formed with arene = benzene (1b), mesitylene (1c), and hexamethylbenzene (1d), although in the last two cases the metallacarborane-carborane species [1-(1′-closo-1′,2′-C2B10H11)-3-(arene)-closo-3,1,2-RuC2B9H10)], 2c and 2d, were also isolated. With the bis(ortho-carborane) transfer reagent [Mg(κ2-2,2′-{1-(1′-closo-1′,2′-C2B10H10)-closo-1,2-C2B10H10)}(DME)2], the target compounds [Ru(κ3-2,2′,3′-{1-(1′-closo-1′,2′-C2B10H10)-closo-1,2-C2B10H10)}(arene)], 4b and 4d, were prepared in reasonable-to-good yields, although for arene = benzene and mesitylene small amounts of the unique paramagnetic species [{Ru(arene)}2(μ-Cl)(μ-κ4-2,2′,3,3′-{1-(1′-closo-1′,2′-C2B10H9)-closo-1,2-C2B10H9})], 3b and 3c, were also formed. In compounds 3, the bis(carborane) acts as a closo-closo-X4(C,C′,B,B′) ligand to the Ru2 unit. In I, 4b, and 4d, the B-agostic B-H?Ru bond is readily cleaved by MeCN, affording compounds [Ru(κ2-2,2′-{1-(1′-closo-1′,2′-C2B10H10)-closo-1,2-C2B10H10})(arene)(NCMe)] (5a, 5b, and 5d) and suggesting that I, 4b, and 4d could act as Lewis acid catalysts, which is subsequently shown to be the case for the Diels-Alder cycloaddition reactions between cyclopentadiene and methacrolein, ethylacrolein and E-crotonaldehyde. All new species were characterized by multinuclear NMR spectroscopy and 1a, 1c, 1d, 2c, 2d, 3b, 3c, 4b, 4d, 5a, 5b, and 5d were also characterized crystallographically.

Chiral Dawson-Type Hybrid Polyoxometalate Catalyzes Enantioselective Diels-Alder Reactions

Can achiral organocatalysts linked to chiral polyanionic metal oxide clusters provide good selectivity in enantioselective C-C bond formations? The answer to this question is investigated by developing a new active hybrid polyoxometalate-based catalyst for asymmetric Diels-Alder reaction. Chirality transfer from the chiral anionic polyoxometalate to the covalently linked achiral imidazolidinone allows Diels-Alder cycloaddition products to be obtained with good yields and high enantioselectivities when using cyclopentadiene and acrylaldehydes as partners.

NOVEL NORBORNENE DERIVATIVE

A novel compound useful as a raw material for a resist material is described. A norbornene derivative having epoxy and a methylene-mediated reactive group in a norbornane skeleton is represented by the following formula. In the formula, R1 represents a hydrogen atom, acryloyl, methacryloyl or hydroxymethylacryloyl, and R2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.

Carbocations as lewis acid catalysts in diels-alder and Michael addition reactions

In general, Lewis acid catalysts are metal-based compounds that owe their reactivity to a low-lying empty orbital. However, one potential Lewis acid that has received negligible attention as a catalyst is the carbocation. We have demonstrated the potential of the carbocation as a highly powerful Lewis acid catalyst for organic reactions. The stable and easily available triphenylmethyl (trityl) cation was found to be a highly efficient catalyst for the Diels-Alder reaction for a range of substrates. Catalyst loadings as low as 500 ppm, excellent yields, and good endo/exo selectivities were achieved. Furthermore, by changing the electronic properties of the substituents on the tritylium ion, the Lewis acidity of the catalyst could be tuned to control the outcome of the reaction. The ability of this carbocation as a Lewis acid catalyst was also further extended to the Michael reaction. Copyright

Diels-alder reaction in air-and moisture-stable zinc-containing ionic liquids

Diels-Alder reactions in a number of air- and moisture-stable dialkylimidazolium halide-ZnCl2 ionic liquids are reported. High yields and high endo selectivities have been observed. The ionic liquids could then be recyclable without loss of reactivity.

Enantioselective catalysts based on the chiral fragment (η5-C5Me5)Ir(Prophos) for Diels-Alder reactions

The aqua complex (SIr,RC)-[(η5-C 5Me5)Ir(Prophos)(H2O)][SbF6] 2 [Prophos = (R)-propane-1,2-diyl-bis(diphenylphosphane)] is an active precursor for the asymmetric Diels-Alder reaction of acyclic enals with cyclopentadiene, 2,3-dimethylbutadiene and isoprene. Enantioselectivities up to 78% ee are achieved. The intermediate Lewis acid-dienophile complex (S Ir,RC)-[(η5-C5Me 5)Ir(Prophos)(ethyl acrolein)][SbF6]2 has been isolated and completely characterized, including the X-ray crystal structure determination. Structural parameters indicate that the disposition of the coordinated dienophile is controlled by CH/π attractive interactions established between a phenyl group of the Prophos ligand and the aldehyde proton of the coordinated enal. Proton NMR data indicate that these interactions are maintained in solution. From diffractometric and spectroscopic data, the origin of the enantioselectivity is discussed.