89873-49-4Relevant academic research and scientific papers
Highly Reactive Metallic Nickel: Reductive Homocoupling Reagent for Benzylic Mono- and Polyhalides
Inaba, Shin-ichi,Matsumoto, Hideyuki,Rieke, Reuben D.
, p. 2093 - 2098 (1984)
Metallic nickel, prepared by the reduction of nickel halides with lithium in glyme using naphthalene as an electron carrier, was found to be a useful reagent for the homocoupling of benzylic mono- and polyhalides.Benzyl halides reacted with metallic nickel at room temperature to give the corresponding 1,2-diarylethanes in good to high yields and functional groups on the aromatic ring such as methoxy, chloro, bromo, nitro, cyano, and alkoxycarbonyl groups were not affected under the conditions employed.Benzylic monohalides (1-(chloromethyl)- or 2-(bromomethyl)naphthalene, chlorodiphenylmethane, and 9-bromofluorene) also underwent coupling reactions with metallic nickel at room temperature to give the corresponding ethane derivatives.On the other hand, benzylic di- and trihalides such as α,α-dibromotoluene and α,α,α-trichlorotoluene yielded mixtures of cis and trans isomers of substituted ethenes.The intermediate of the reaction, benzylnickel complex, was trapped with electron deficient olefins such as methyl acrylate and acrylonitrile.
Chromium(II)-Mediated Intermolecular Free-Radical Carbon-Carbon Bond Formation
Tashtoush, Hasan I.,Sustmann, Reiner
, p. 287 - 289 (2007/10/02)
Chromium(II) complexes are found to be effective mediators for intermolecular free-radical C-C bond formation.Thus, Cr(en)2(2+) species react with alkyl halides to generate the corresponding alkyl radicals which are readily trapped with electron-deficient alkenes to afford the coupling products.Key Words: Radicals / Bond formation, C-C / Chromium(II) complexes
CYANOETHYLATION OF HYDROCARBONS, INITIATED BY AUTOOXIDATION
Galust'yan, G. G.
, p. 811 - 815 (2007/10/02)
Oxygen was used as an initiator of the free-radical cyanoethylation of alkylbenzenes (toluene, o-, m-, and p-xylenes, mesitylene, ethylbenzene, p-cymene) and tetralin (0.25-0.66 liter of oxygen to 1 liter of the hydrocarbon) The reactions were carried out in an autoclave at 150-350 deg C with a carbon-acrylonitrile ratio of 100:1.The initiation evidently results mainly from homolytic dissociation of the hydroperoxide formed during the autooxidation of the hydrocarbons.The effectiveness of oxygen for the initiation of the cyanoethylation of hydrocarbons depends on the oxidizability of the hydrocarbons.
