40856-16-4

Upstream product

• 111-71-7 heptanal 
• 372-09-8 cyanoacetic acid 
• 111-66-0 oct-1-ene 
• 506-77-4 cyanogen chloride 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 74-90-8 hydrogen cyanide 
• 629-05-0 n-octyne 
• 544-92-3 copper(I) cyanide 
• 42599-17-7 (E)-1-iodo-1-octene 
• 1122-85-6 phenyl cyanate 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 75-52-5 nitromethane 

Relevant academic research and scientific papers

PROCESS FOR HYDROCYANATION OF TERMINAL ALKYNES

The present invention refers to a process for a Rh-catalyzed Anti-Markovnikov hydrocyanation of terminal alkynes which process discloses, for the first time, the highly stereo- and regio-selective hydrocyanation of terminal alkynes to furnish E- configured alkenyl nitriles and the catalyst used in the present process.

Rh-Catalyzed Anti-Markovnikov Hydrocyanation of Terminal Alkynes

We report the first highly stereo- and regioselective hydrocyanation of terminal alkynes to furnish E-configured alkenyl nitriles. Acrylonitriles can be accessed on gram scale with broad substrate scope and functional group tolerance. The hydrocyanation reaction employs acetone cyanohydrin as a practical alternative to HCN gas.

Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs' catalysts

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.

Solid-phase synthesis of (E)-3-substituted acrylonitriles from polystyrene-supported α-selenoacetonitrile

A facile method for solid-phase organic synthesis of (E)-3-substituted acrylonitriles in good yields using polystyrene-supported α- selenoacetonitrile has been developed. The advantages of this method include straightforward operation, lack of odor, good

Highly active ruthenium-based catalyst for metathesis of cyano-contained olefins

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

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

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

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

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.

Tandem oxidation processes: The direct conversion of activated alcohols into nitriles

The direct conversion of primary alcohols into nitriles is reported (RCH2OH into RCN) using manganese dioxide and ammonia in 2-propanol - THF, containing magnesium sulfate at room temperature. This transformation, which proceeds via an in situ