7167-28-4Relevant articles and documents
Total Synthesis of (±)-2-Isocyanoallopupukeanane
Ho, Tse-Lok,Kung, Liang-Ren,Chein, Rong-Jie
, p. 5774 - 5779 (2000)
2-Isocyanoallopupukeanane (4) has been obtained in racemic form from methyl 2-exo-methylbicyclo-[2.2.1]hept-5-ene-2-endo-carboxylate via dibromocarbene addition, SN2′ displacement, chain extension, and elaboration of the unsaturated ketone 12c which underwent an intramolecular hetero-Diels-Alder reaction to afford 13 containing all the skeletal carbon atoms. The dihydropyran unit was cleaved by ozonolysis to give the tricarbocyclic intermediate which required seven more steps to complete the synthesis.
Effect of Microemulsions on the Diels-Alder Reaction: Endo/Exo Ratios in the Reaction of Cyclopentadiene and Methyl Methacrylate
Gonzalez, Alvaro,Holt, Smith L.
, p. 3186 - 3188 (1982)
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Stereoselective synthesis of 2-isocyanoallopupukeanane
Ho, Tse-Lok,Kung, Liang-Rern
, p. 1051 - 1052 (1999)
(matrix presented) A stereoselective synthesis of 2-isocyanoallopupukeanane (3) in ca, 5% overall yield features an intramolecular Diels-Alder reaction to establish a bridged cyclopentane ring to the existing bicyclo[3.2.1]octane unit.
Hydrogen-bond-rich ionic liquids as effective organocatalysts for Diels-Alder reactions
Erfurt, Karol,Wandzik, Ilona,Walczak, Krzysztof,Matuszek, Karolina,Chrobok, Anna
, p. 3508 - 3514 (2014/07/08)
The synthesis and characterisation of new hydrogen-bond-rich ionic liquids and studies of their catalytic performance in Diels-Alder reactions are described. d-Glucose and chloroalcohols were used as the raw materials and as the sources of hydroxyl groups for the synthesis of ionic-liquid cations, whereas weakly coordinating bis(trifluoromethylsulfonyl)imide was used as the anion. The new ionic liquids were analysed by 1H and 13C NMR spectroscopy and by ESI-MS experiments, which confirmed their structures. In addition, the thermal data of the studied ionic liquids measured by differential scanning calorimetry and thermogravimetric analysis showed that these compounds tend to form a glass at temperatures in the range of -29°C to -16°C and are thermally stable from ambient temperature to at least 430°C, most likely because of the presence of bis(trifluoromethylsulfonyl) imide anions. The performance of the ionic liquids in the model reaction of cyclopentadiene with diethyl maleate or methyl acrylate was investigated. The studied ionic liquids showed high activity even when present in catalytic amounts (4 mol% with respect to the dienophile). An increase in the number of hydroxyl groups present in the ionic liquid structure resulted in higher reaction rates. This journal is the Partner Organisations 2014.
Nanoporous solid acid catalyst for the Diels-Alder reaction of 1,3-dienes with acrylates
Onaka, Makoto,Hashimoto, Naoki,Yamasaki, Ryota,Kitabata, Yasuyoshi
, p. 166 - 167 (2007/10/03)
Nanoporous aluminosilicate, Al-HMS with a high aluminum content, strong acidity, and nanoporosity was found to catalyze the Diels-Alder reaction of 1,3-dienes with methacrylate and acrylate, and turned out to be a green alternative to homogeneous acid catalysts.