40856-15-3Relevant articles and documents
Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs' catalysts
Rountree, Sandra M.,Taylor, Sarah F.R.,Hardacre, Christopher,Lagunas, M. Cristina,Davey, Paul N.
, p. 94 - 104 (2015/09/28)
A series of α,β-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs' catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest, as it has not previously being used as a substrate in cross-metathesis reactions and allows access to valuable intermediates for the synthesis of new fragrances. Most reactions gave good selectivity of the desired CM product (≥90%). Detailed optimisation and mechanistic studies have been performed on the cross-metathesis of acrolein with 1-decene. Recycling of the catalyst has been attempted using ionic liquids.
Highly active ruthenium-based catalyst for metathesis of cyano-contained olefins
Zhang, Wenzhen,Zhang, Rong,He, Ren
, p. 4203 - 4205 (2008/02/05)
Ruthenium benzylidene complex (H2IMes)(2-CH3-C5H4N)(Cl)2Ru{double bond, long}CHPh [H2IMes = 1,3-bis(2,6-dimethylphenyl)-4,5-dihydroimidazol-2-ylidene] (4), which introduced ortho substituted pyridine as dissociating ligand to weaken Ru-N bond and accelerate initiation through steric hindrance, was prepared by the reaction of (H2IMes)(PPh3)(Cl)2Ru{double bond, long}CHPh (1) with 2-methylpyridine and proved to exhibit enhanced catalytic activity for cyano-contained olefin metathesis.
Benzylideneruthenium complexes bearing pyridine-based ligands and their influence on the formation of mono- or bis(pyridine) complexes
Zhang, Wen-Zhen,He, Ren,Zhang, Rong
, p. 5345 - 5352 (2008/09/17)
Benzylideneruthenium complexes bearing the N-heterocyclic carbene (NHC) ligand 1,3-bis(2,6-dimethylphenyl)-4,5-dihydroimidazol-2-ylidene (H 2IMe) and one or two pyridine-based ligands have been prepared by treating [RuCl2-(=CHPh) (H
Indium(I) bromide-mediated coupling of dibromoacetonitrile with aldehydes followed by Boord elimination of bromine and oxygen of β-bromo alkoxides for preparation of 3-organyl-2-alkenenitriles
Peppe, Clovis,de Azevedo Mello, Paola,das Chagas, Rafael Pav?o
, p. 2335 - 2339 (2007/10/03)
The organoindium compound derived from indium monobromide and dibromoacetonitrile reacts with carbonyl compounds to afford the corresponding 2-bromo-2-cyano-indium(III) alkoxide. The action of a second equivalent of indium monobromide onto the alkoxides derived from aldehydes promotes the Boord elimination of the β-related oxygen and bromine atoms leading to 2-alkenenitriles.
PROCESS FOR MAKING FATTY ACID NITRILES AND FATTY AMINES BY CROSS-METATHESIS OF NORMAL ALPHA OLEFINS
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Page 12, (2008/06/13)
A process for preparing fatty amines by the cross-metathesis of normal alpha olefins and acrylonitrile to form an intermediate fatty acid nitrile which is hydrogenated to the corresponding fatty amine.
Unsaturated nitriles: Stereoselective MgO eliminations
Fleming, Fraser F.,Shook, Brian C.
, p. 3668 - 3672 (2007/10/03)
α,β-Unsaturated nitriles are readily synthesized by eliminating MgO from β-hydroxynitriles. Deprotonating acyclic, and cyclic, β-hydroxynitriles with excess MeMgCl smoothly generates dianion intermediates that eject MgO with concurrent formation of α,β-unsaturated nitriles. Alternatively, sequential addition of lithioacetonitrile and MgBr2 to aldehydes and ketones generates magnesium alkoxides in situ that eliminate MgO upon addition of MeMgCl. The MeMgCl-induced MgO eliminations smoothly generate α,β-unsaturated nitriles from hindered ketones that are otherwise difficult to synthesize.
Polymer-supported Phosphonates. Olefins from Aldehydes, Ketones, and Dioxolans by means of Polymer-supported Phosphonates
Cainelli, Gianfranco,Contento, Michele,Manescalchi, Francesco,Regnoli, Rodolfo
, p. 2516 - 2519 (2007/10/02)
Phosphonates substituted with electron-withrdrawing groups (CN and CO2Me) have been supported, by means of a neutralization reaction, on the macroreticular anion-exchange resin Amberlyst A-26.Treatment of carbonyl compounds with the polymer-bound phosphonate in various solvents gave olefins in high yields, at room temperature.Either batch or column techniques are employed, the latter offering the opportunity of a continuous procedure.The simultaneous use of the phosphonate resin and of an acidic one (Amberlyst 15 H) allowed the direct sequential hydrolysis and olefination of dioxolans.
