Clean Synthesis in Water: Darzens Condensation Reaction of Aromatic Aldehydes with Phenacyl Chloride
作者： Shi Da-Qing , Zhang Shu , Zhuang Qi-Ya , Wang Xiang-Shan , Tu Shu-Jiang
关键词:
摘要: The Darzens condensation reaction of aromatic aldehydes with phenacyl chloride proceeded very efficiently in a water suspension medium the presence triethylbenzylammonium and only trans-2, 3-epoxy-l, 3-diaryl-l-propanones were formed which can be isolated simply by filtration. structures these compounds confirmed elemental analysis, IR 1H NMR spectra. Their configurations are agreement that same reported literature. Compared to classical condensation, this new method has advantages good yields, high stereoselectivity, low running cost inexpensive environmentally benign procedure.
sci-hub.se 参考文章(18)
J. Seyden-Penne, M.C. Roux-Schmitt, A. Roux, Effet de solvant sur le bilan stéréochimique de la réaction de darzens—I Tetrahedron. ,vol. 26, pp. 2649- 2656 ,(1970) , 10.1016/S0040-4020(01)92839-X
Darryl C. Rideout, Ronald Breslow, Hydrophobic acceleration of Diels-Alder reactions Journal of the American Chemical Society. ,vol. 102, pp. 7816- 7817 ,(1980) , 10.1021/JA00546A048
Franca Bigi, Silvia Carloni, Leonetto Ferrari, Raimondo Maggi, Alessandro Mazzacani, Giovanni Sartori, Clean synthesis in water. Part 2: Uncatalysed condensation reaction of Meldrum's acid and aldehydes Tetrahedron Letters. ,vol. 42, pp. 5203- 5205 ,(2001) , 10.1016/S0040-4039(01)00978-9
Roberto Ballini, Giovanna Bosica, The Michael reaction of nitroalkanes with conjugated enones in aqueous media Tetrahedron Letters. ,vol. 37, pp. 8027- 8030 ,(1996) , 10.1016/0040-4039(96)01816-3
Frank W. Bachelor, R. K. Bansal, Darzens glycidic ester condensation Journal of Organic Chemistry. ,vol. 34, pp. 3600- 3604 ,(1969) , 10.1021/JO01263A082
Francesco Fringuelli, Oriana Piermatti, Ferdinando Pizzo, Luigi Vaccaro, Recent Advances in Lewis Acid Catalyzed Diels−Alder Reactions in Aqueous Media European Journal of Organic Chemistry. ,vol. 2001, pp. 439- 455 ,(2001) , 10.1002/1099-0690(200102)2001:3<439::AID-EJOC439>3.0.CO;2-B
Franca Bigi, Luca Chesini, Raimondo Maggi, Giovanni Sartori, Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids. Journal of Organic Chemistry. ,vol. 64, pp. 1033- 1035 ,(1999) , 10.1021/JO981794R
I. Amato, The slow birth of green chemistry. Science. ,vol. 259, pp. 1538- 1541 ,(1993) , 10.1126/SCIENCE.259.5101.1538
Chao Jun. Li, Organic reactions in aqueous media - with a focus on carbon-carbon bond formation Chemical Reviews. ,vol. 93, pp. 2023- 2035 ,(1993) , 10.1021/CR00022A004
Francesco Fringuelli, Giosanna Pani, Oriana Piermatti, Ferdinando Pizzo, Condensation reactions in water of active methylene compounds with arylaldehydes. One-pot synthesis of flavonols. Tetrahedron. ,vol. 50, pp. 11499- 11508 ,(1994) , 10.1016/S0040-4020(01)89287-5