18670-23-0

Upstream product

• 140-29-4 phenylacetonitrile 
• 67-64-1 acetone 
• 41658-69-9 2-bromo-2-methyl-propionitrile 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 
• 151-50-8 potassium cyanide 
• 327619-21-6 thiophosphoric acid S-(1,1-dimethyl-2-oxo-2-phenylethyl) ester O,O-diethyl ester 
• 7677-24-9 trimethylsilyl cyanide 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 673-32-5 1-Phenylprop-1-yne 
• 75-05-8 acetonitrile 
• 98-88-4 benzoyl chloride 
• 611-70-1 phenyl isopropyl ketone 
• 86108-36-3 Toluene-4-sulfonic acid 2-cyano-2,2-dimethyl-1-phenyl-ethyl ester 
• 24425-12-5 (α,α-Dimethylphenacyl)-triphenylphosphoniumiodid 

Downstream Products

• 4412-08-2 3-methyl-2-phenylbut-2-enoic acid 
• 7465-12-5 3-methyl-2-phenylbut-2-enamide 

Relevant academic research and scientific papers

A synthetic approach to tetrasubstituted alkenes: Using β-carbonyl benzothiazol-2-yl sulfones as electrophiles

A novel olefination method based on the modified Julia olefination reaction was developed. The reactions of β-carbonyl benzothiazol-2-yl sulfones with a series of alkynyllithiums and TMSCN gave the corresponding β-alkoxy sulfone intermediates, which under

Nickel/Lewis acid-catalyzed carbocyanation of alkynes using acetonitrile and substituted acetonitriles

Nickel/Lewis acid dual catalysis is found to effect the carbocyanation reaction of alkynes using acetonitrile and substituted acetonitriles to give a range of variously substituted acrylonitriles. The addition of propionitrile across alkynes is also demonstrated briefly to give the corresponding ethylcyanation products in good yields, whereas the reaction of butyronitrile gives significant amounts of hydrocyanation products due possibly to β hydride elimination of a propylnickel intermediate. The reaction of optically active α phenylpropionitrile suggests a reaction mechanism that involves oxidative addition of a CCN bond with retention of its absolute configuration.

A general and stereoselective method for synthesis of tri- and tetrasubstituted alkenes

A convenient, general and stereoselective synthesis of trisubstituted alkenes and tetrasubstituted alkenes containing a cyanide function as well as trisubstituted episulphides have been elaborated. Methodology described for the preparation of these compounds is based on the corresponding readily available selenophosphates 1 and thiophosphates 2.

Alkylation of Nitrile Anions by Tertiary α-Halo Ketones and Nitriles

Potassium salts of nitriles bearing carbethoxy, cyano, or phenyl groups at the α carbon react with tertiary α-halo ketones and nitriles (1-5) in DMSO or HMPA to provide the alkylated β-keto- or β-cyano-β,β-dialkyl nitriles 6-10 in useful yields. (PhCHCN)(-) undergoes cyclization with p-XC6H4COCCl(CH3)2 to produce 2(5H)-furanone 11.Reaction of (Ph2CCN)(-) with PhCOCCl(CH3)2 affords the hydrolyzed ketone 12a and recovered carbon acid, while the anion undergoes oxidative dimerization to NCCPh2CPh2CN with p-O2NC6H4COCCl(CH3)2 with concomitant formation of the reduced ketone p-O2NC6H4COCH(CH3)2 and the hydrolyzed ketone 12b.The alkylations of (-) and (-) with p-O2NC6H4COCX(CH3)2 take place by the SRN1 process.

AN INTERPRETATION OF THE SUBSTITUENT EFFECT IN THE BLAISE REARRANGEMENT IN TERMS OF PI-ORBITALS

The migratory aptitude of the substituent groups in the Blaise rearrangement can be explained in terms of the pi-electronic properties of the groups in the highest occupied molecular orbitals.The rates of the rearrangement reaction with relation to the substituent groups were also rationally understood based on the energy levels of the molecular orbitals.

HYDROGENATION REACTIONS WITH HYDRIDOCOBALT TETRACARBONYL

The tetrasubstituted ethylene, bifluorenylidene, reacts very rapidly (4.06*10-2 l mol-1 sec-1 at 0 deg C) with HCo(CO)4 to give bifluorenyl. α-Phenylacrylonitrile (atroponitrile) reacts even more rapidly under the same conditions (6.0 l mol-1 sec-1).Other highly substituted ethylenes react very slowly with HCo(CO)4, indicating considerable steric effects.The data are consistent with radical type intermediates.

Preparation of nitriles

α,β-Unsaturated nitriles are prepared from carbonyl compounds and then reduced by reaction with an alkanol and magnesium in the presence of an ammonium salt.