53153-76-7Relevant articles and documents
Amination of Carbenium Ions Generated by Directed Protonolysis of Cyclopropane
Skvorcova, Marija,Lukasevics, Lukass T.,Jirgensons, Aigars
, p. 3780 - 3792 (2019/03/29)
Directed intramolecular protonolyis of the cyclopropane C-C bond is demonstrated as a strategy to generate carbenium ions. This intermediate can be subjected to amination with nitriles under Ritter reaction conditions. Directing groups such as carbamate, carboxamide, urea, ester, and ketone were found to be efficient for regioselective anti-Markovnikov cleavage of cyclopropane. Depending on the directing group, the amination provided orthogonally protected 1,4-diamine, ?-amino carboxylic, and ?-amino ketone derivatives.
Convenient procedure of Horner-Wadsworth-Emmons olefination for the synthesis of simple and functionalized α,β-unsaturated nitriles
Lattanzi, Alessandra,Orelli, Liliana R.,Barone, Patrizia,Massa, Antonio,Iannece, Patrizia,Scettri, Arrigo
, p. 1333 - 1337 (2007/10/03)
A mild and practical procedure of Horner-Wadsworth-Emmons olefination promoted by lithium hydroxide and α-cyano phosphonates has been set up for the synthesis of α,β-unsaturated nitriles. The reaction conditions are tolerated by functionalized ketones and the exclusive formation of E-γ-hydroxy α,β-unsaturated nitriles has been observed.
Substitution and Elimination Reactions via One Electron Transfer Process. A New Olefin Synthesis from β-Nitro Sulfones
Ono, Noboru,Tamura, Rui,Nakatsuka, Tamon,Hayami, Jun-ichi,Kaji, Aritsune
, p. 3295 - 3300 (2007/10/02)
gem-Bromonitro compounds or gem-dinitro compounds couple with carbanions derived from α-cyano sulfones or α-carbonyl sulfones to give β-nitro sulfones.The nitro and sulfonyl groups are eliminated from the coupling products on treatment with reductive one electron transfer reagents to give α,β-unsaturated carbonyl compounds or nitriles.
