2097-72-5Relevant articles and documents
Facile syntheses of homoleptic diarylmercurials via arylboronic acids
Partyka, David V.,Gray, Thomas G.
, p. 213 - 218 (2009/04/13)
A general procedure for the syntheses of diarylmercurials is presented. Reactions proceeded in isopropanol in the presence of a base and arylboronic acid. With one exception, all reactions proceeded in good to excellent yields, and this procedure was appl
Electrochemical Reduction of 4-Iodo- and 4-Bromoanisole at Mercury and Carbon Cathodes in Dimethylformamide
Mubarak, Mohammad S.,Karras, Louis L.,Murcia, Noel S.,Bart, John C.,Stemple, Joseph Z.,Peters, Dennis G.
, p. 1065 - 1070 (2007/10/02)
In dimethylformamide containing tetramethylammonium perchlorate, cyclic voltammograms for reduction of 4-iodo- and 4-bromoanisole at mercury and carbon electrodes exhibit single irreversible waves corresponding formally to two-electron cleavage of the carbon-halogen bond.In preparative-scale controlled-potential electrolyses of 4-iodoanisol at mercury pool cathodes, a two-to-one mixture of anisole and bis(p-anisyl)mercury is obtained at potentials close to the peak potential, whereas anisole is the only species formed at more negative potentials.Reduction of 4-iodoanisole at mercury appears to proceed via p-anisyl radicals that (i) yields adsorbed p-anisylmercury radicals which disproportionate to give bis(p-anisyl)mercury or (ii) undergo further reduction, followed by protonation, to afford anisole.Electrolyses of 4-iodoanisole at carbon electrodes, as well as reduction of 4-bromoanisole at both mercury and carbon, result solely in the production of anisole; presumably, even if p-anisyl radicals are generated transiently, they undergo facile reduction to p-anisyl carbanions, which are protonated immediately to yield anisole.
Electrochemical Reduction of Unsymmetrically Substituted Diphenyliodonium Salts at Mercury Cathodes in Dimethylformamide
Mubarak, Mohammad S.,Peters, Dennis G.
, p. 673 - 677 (2007/10/02)
A study has been made of the electrochemistry of five unsymmetrically substituted diphenyliodonium salts at mercury cathodes in dimethylformamide containing tetramethylammonium perchlorate.Polarograms indicate that the iodonium cations undergo reduction in three stages: (1) one-electron reduction to yield either (a) iodobenzene and a substituted phenylmercury radical or (b) a substituted iodobenzene and a phenylmercury radical, (2) two-electron reduction of the iodobenzene or substituted iodobenzene, and (3) one-electron reduction of the substituted or unsubstituted phenylmercury radical.When electrolyses are performed at potentials corresponding to the first stage of reduction, electron-withdrawing substituents induce the production of more iodobenzene than substituted iodobenzene, whereas electron-releasing groups favor the formation of less iodobenzene than substituted iodobenzene; the other major products (diphenylmercury and symmetrically disubstituted diphenylmercury) arise via disproportionation of adsorbed phenylmercury radicals.At potentials corresponding to the second stage of reduction, electrolyses yield benzene, substituted benzene, and diorganomercury compounds; at potentials corresponding to the third stage of reduction, benzene and substituted benzene are formed.
