71750-16-8Relevant academic research and scientific papers
Reaction of the electrogenerated cyanomethyl anion with carbonyl compounds: A clean and safe synthesis of β-hydroxynitriles
Bianchi, Gabriele,Feroci, Marta,Rossi, Leucio
experimental part, p. 3863 - 3866 (2010/01/11)
The electrogenerated cyanomethyl anion reacts with carbonyl compounds to yield the corresponding β-hydroxymtriles in moderate to high yields. The reported methodology is very clean and safe, avoiding the use of any classical base or catalyst.
SmI2-mediated nitrile aldol reaction
Caracoti, Andrei,Flowers II, Robert A.
, p. 3039 - 3041 (2007/10/03)
The SmI2-mediated coupling of α-bromoacetonitrile and α- bromopropionitrile with aliphatic ketones and aldehydes produces β- hydroxynitriles in good yields. Reactions typically proceed with little diastereoselectivity, but selectivity enhanceme
Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles
Shono, Tatsuya,Kise, Naoki,Fujimoto, Taku,Tominaga, Naoto,Morita, Hiroshi
, p. 7175 - 7187 (2007/10/02)
Electroreduction of γ- and δ-cyano ketones in i-PrOH with Sn cathode gave α-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products.Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of γ- and δ-cyano ketones in one of the key steps.Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product.The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
Formation and efficient addition of cerium(III) derivative of acetonitrile to ketones
Liu,Al-Said
, p. 5473 - 5476 (2007/10/02)
The cerium(III) derivative of acetonitrile undergoes addition with ketones efficiently. It adds effectively to hindered ketones and gives 1,2-adduct exclusively with conjugated enones.
Stereochimie de l'addition des α-carbanions des nitriles, esters et amides N,N-disubstitues sur la tertio butyl-4 cyclohexanone dans l'ammoniac liquide
Dobrev, Alexandre,Ivanov, Christo,Lattes, Armand,Bon, Maryse
, p. 1084 - 1088 (2007/10/02)
Starting from the hypothesis that the structure of a carbanion influences the stereochemistry of their addition on to carbonyl derivatives, we synthesized various functionalised α carbanions. - For the addition of nitrile anions on 4-t-butyl-cyclohexanone in liquid ammonia, the stereoselectivity depends on the carbeniate structure of the carbanion, but other factors are also operating. - With α,α-disubstituted nitriles the stereoselectivity is surprisingly very high.Cyclic nitriles give different diasteromers depending on the ring strain.Using t-butyl esters we observe a lower stereoselectivity: with α,α-disubstituted esters the diastereomeric ratio is nearly one. - N,N-dibstituted amides have a similar behaviour as in HMPT.With N-phenyl amides yields and stereoselectivities are higher. - In all cases, the axial attack is favored when steric factors are small.When the equatorial attack is predominant, it is possible to correlate this orientation with the predominating enolate structure of the carbanion with a phenyl group in the α position. - A special attention is focussed on N-aryl acetamides where electronic effects can be important, and also on steric effects caused by α-substitution.
