83188-08-3Relevant academic research and scientific papers
Ionic liquids made with dimethyl carbonate: Solvents as well as boosted basic catalysts for the michael reaction
Fabris, Massimo,Lucchini, Vittorio,Noe, Marco,Perosa, Alvise,Selva, Maurizio
experimental part, p. 12273 - 12282 (2010/06/11)
This article describes 1) a methodology for the green synthesis of a class of methylammonium and methylphosphonium ionic liquids (ILs), 2) how to tune their acid-base properties by anion exchange, 3) complete neat-phase NMR spectroscopic characterisation
Bifunctional heterogeneous catalysis of silica-alumina-supported tertiary amines with controlled acid-base interactions for efficient 1,4-addition reactions
Motokura, Ken,Tanaka, Satoka,Tada, Mizuki,Iwasawa, Yasuhiro
experimental part, p. 10871 - 10879 (2010/04/05)
We report the first tunable bifunctional surface of silica-aluminasupported tertiary amines (SA-NEt2) active for catalytic 1,4-addition reactions of nitroalkanes and thiols to electron-deficient alkenes. The 1,4-addition reaction of nitroalkanes to electron-deficient alkenes is one of the most useful carbon-carbon bond-forming reactions and applicable toward a wide range of organic syntheses. The reaction between nitroethane and methyl vinyl ketone scarcely proceeded with either SA or homogeneous amines, and a mixture of SA and amines showed very low catalytic activity. In addition, undesirable side reactions occurred in the case of a strong base like sodium ethoxide employed as a catalytic reagent. Only the present SA-supported amine (SA-NEt2) catalyst enabled selective formation of a double-alkylated product without promotions of side reactions such as an intramolecular cyclization reaction. The heterogeneous SA-NEt2 catalyst was easily recovered from the reaction mixture by simple filtration and reusable with retention of its catalytic activity and selectivity. Fur-thermore, the SA-NEt2 catalyst system was applicable to the addition reaction of other nitroalkanes and thiols to various electron-deficient alkenes. The solid-state magic-angle spinning (MAS) NMR spectroscopic analyses, including variable-contact-time 13C cross-polarization (CP)/MAS NMR spectroscopy, revealed that acid-base interactions between surface acid sites and immobilized amines can be controlled by pretreatment of SA at different temperatures. The catalytic activities for these addition reactions were strongly affected by the surface acid-base interactions. 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
The Michael reaction of nitroalkanes with conjugated enones in aqueous media
Ballini, Roberto,Bosica, Giovanna
, p. 8027 - 8030 (2007/10/03)
The Michael reaction of various nitroalkanes with conjugated enones can be performed in NaOH 0.025 M and in the presence of cetyltrimethylammonium chloride (CTACl) as cationic surfactant, without any organic solvent. Good yields of the products are obtained even with hindered starting materials.
The Synthesis of 1,4-Diketones via Fluoride-catalysed Michael Addition and Supported-permanganate-promoted Nef Transformation
Clark, James H.,Cork, David G.,Gibbs, Hugh W.
, p. 2253 - 2258 (2007/10/02)
A versatile synthetic route for the preparation of 1,4-diketones from simple starting materials is described and applied to the preparation of a wide range of diketones.The two most important steps in the reaction are the fluoride ion-catalysed Michael addition of a nitroalkane to a vinyl ketone and the subsequent transformation of the nitro ketone to the diketone using supported permanganate as the oxidant.The interaction of F- with nitroethane has been studied and a number of sources of F- have been tested in the Michael addition reaction.Potassium fluoride supported on alumina and potassium permanganate supported on silica gel are remarkably efficient reagents for the Michael addition and Nef transformation stages, respectively, although it is important to determine the best reagent loadings and drying conditions for maximum reaction efficiency to be achieved.
Synthesis of 1,4-Diketones by Fluoride-catalysed Michael Addition and Supported Permanganate Oxidation
Clark, James H.,Cork, David G.
, p. 635 - 636 (2007/10/02)
A wide variety of 1,4-diketones may be prepared from simple starting materials by using fluoride ion-catalysed Michael additions and silica gel-supported permanganate-promoted Nef transformations.
