53153-76-7Relevant academic research and scientific papers
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.
Non-reductive decyanation reactions of disubstituted malononitrile derivatives promoted by NaHMDS
Domon, Daisuke,Iwakura, Masaru,Tanino, Keiji
, p. 1957 - 1960 (2017/04/27)
A new method for achieving the decyanation of disubstituted malononitrile derivatives without using reducing agents has been developed. Treatment of a six-membered malononitrile derivative with NaHMDS followed by methanol afforded the corresponding acetonitrile derivative in high yield. The present method was applicable to the decyanation reactions of a variety of malononitriles including four- and five-membered compounds as well as acyclic ones.
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.
FREE RADICAL CHAIN ELIMINATION REAKTION (ERC1). CONVERSION OF VICINAL DINITRO COMPOUNDS OR β-NITRO SULFONES TO OLEFINS WITH TRIBULYLTIN HYDRIDE
Ono, Noboru,Miyake, Hideyoshi,Tamura, Rui,Hamamoto, Isami,Kaji, Aritsune
, p. 1139 - 1142 (2007/10/02)
Vicinal dinitro compounds (1) or β-nitro sulfones (2) are converted to olefins in good yields on treatment with tributyltin hydride.This elimination proceeds by way of an electron transfer chain mechanism.The elimination from 1 is nonstereospecific and the elimination from 2 is stereospecific.
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.
