Diphenyliodonium Salts Research Articles

The formation of triarylsulfonium salts through a photochemical route

An original method of synthesizing triarylsulfonium salts through UV light excitation of diphenylsulfides in presence of diphenyliodonium salts is described.

Synthesis and characterization of photosensitive polyimides

AbstractAll aromatic polyimides bearing diarylsulfide linkages in the main chain were prepared either by condensation of a sulfur containing dianhydride with an aromatic diamine or the condensation of a sulfur containing aromatic diamine with a dianhydride. Phenylation with diphenyl iodonium salts was then used to convert the diarylsulfide groups to triarylsulfonium salts. The resulting photosensitive polyimides were shown to undergo main chain cleavage during photolysis using UV irradiation. These new polyimides are candidates for positive working, high temperature photoresist materials.

Pulse radiolysis study of the formation of aromatic radical cations enhanced by diphenyliodonium salts

Further pulse radiolysis investigations of the formation of the biphenyl radical cation enhanced by diphenyliodonium salts in dichloromethane solution are reported. The slow formation of the radical cation in the presence of Ph/sub 2/IPF/sub 6/ (or Ph/sub 2/IAsF/sub 6/) is also observed in 1,2-dichloroethane but not in acetone, acetonitrile, and ethyl acetate. It was suggested that the free radicals generated from the chlorohydrocarbon solvents are largely responsible for the slow formation of the radical cation. Results with naphthalene, anthracene, and pyrene are also presented. The contribution of the excited states of the aromatic compounds, which have been proposed to be the precursors of the radical cations by a photolysis study, is not important in the pulse radiolysis. The effects of the salts in the radiolysis are compared with those in the photolysis.

Curing of epoxy resins with diphenyliodonium salts as thermal initiators

AbstractThe curing reaction of a thermally curable epoxy system containing diphenyliodonium hexafluoroarsenate was investigated by using the dynamic and isothermal techniques of differential scanning calorimetry (DSC). It was shown that the curing involved two consecutive reactions. The heat of the total curing reaction and overall kinetic parameters for the two reactions were obtained.

Electrochemical reduction of unsymmetrically substituted diphenyliodonium salts at mercury cathodes in dimethylformamide

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTElectrochemical reduction of unsymmetrically substituted diphenyliodonium salts at mercury cathodes in dimethylformamideMohammad S. Mubarak and Dennis G. PetersCite this: J. Org. Chem. 1985, 50, 5, 673–677Publication Date (Print):March 1, 1985Publication History Published online1 May 2002Published inissue 1 March 1985https://doi.org/10.1021/jo00205a024RIGHTS & PERMISSIONSArticle Views102Altmetric-Citations21LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (676 KB) Get e-Alerts Get e-Alerts

Kationische Photopolymerisation von Isobutylglycidether mit Benzoinderivat/Aryloniumsalz‐ bzw. Benzildimethylketal/Aryloniumsalz‐Initiatorsystemen

Cationic Photopolymerization of Isobutylglycidyl Ether with Benzoine Derivatives/Arylonium Salts‐ or Benzildimethyl Ketal/Arylonium Salts‐Initiator SystemsRadicals produced by photolysis of benzoine derivatives and benzile dimethylketale decompose arene diazonium salts (ArN2⊕), diphenyliodonium salts (Ph2I⊕) and triphenylsulfonium salts (Ph3S⊕), respectively. The carbenium ions or protons formed in this way can be used for the cationic polymerization of isobutylglycidyl ether (IBGE). The efficiency of this polymerization depends on the quantum yields of the onium salts decomposition. A reactivity ArN2⊕ > Ph2I⊕ > Ph3S⊕ was found. In the case of ArN2⊕ the salt decomposition is caused by electron transfer between the photolytically produced substituted benzylic radicals and the diazonium ions. It is assumed that by the decomposition of Ph2I⊕ and Ph3S⊕ intermediates occur, which give rise to some reversible reactions. Therefore, the quantum yields of onium salt decomposition are less than those of initiator photolysis. The rate of cationic polymerization of IBGE is also influenced by the anion of onium compounds. A sequence PF6⊖ >SbF6⊖ >BF4⊖ was found.

Photoinitation of cationic polymerization. II. Laser flash photolysis of diphenyliodonium salts

AbstractLaser flash photolysis of diphenyliodonium salts produces phenyliodinium radical cation (PhI+·), which was also generated independently by flash‐induced electron transfer from iodobenzene to a phenanthrolinium salt. Apparent second‐order rate constants were determined for reaction of the transient (PhI+·) with nucleophiles, including iodobenzene and cyclohexene oxide. Quantum yields of formation of acid from stationary photolysis of diphenyliodonium hexafluoroarsenate were found to be significantly higher than yields of iodobenzene. These results may be explained by facile reaction of PhI+· with PhI to yield a new iodonium salt together with a proton. High reactivity of PhI+· with cyclohexene oxide suggests that the transient may directly initiate cationic polymerization of epoxides.

Electrochemical reduction of diphenyliodonium salts and phenyl mercuric halides in dimethylformamide

Electrochemical reduction of diphenyliodonium salts and phenyl mercuric halides in dimethylformamide

Electrochemical reduction of diphenyliodonium salts and phenyl mercuric halides in dimethylformamide

Pulse polarograms for reduction of diphenyliodonium halides in dimethylformamide containing tetramethylammonium perchlorate exhibit either three or four waves, depending on the concentrations of supporting electrolyte and starting material. In the presence of 0.1 M tetramethylammonium perchlorate, diphenyliodonium bromide exhibits three waves (I, II, and III) when the concentration of starting material is lower than 0.74 m M; for higher concentrations of diphenyliodonium bromide, the first wave splits and the pulse polarogram consists of four waves (Ia, Ib, II, and III). For electrolyses of diphenyliodonium bromide at potentials corresponding to either wave Ia or wave, Ib, diphenylmercury and iodobenzene are obtained and the coulometric n value is unity. At potentials on wave II, diphenylmercury and benzene are formed and the n value is three. For electrolyses done at potentials on wave III, the yields of benzene and diphenylmercury as well as the n value are potential dependent. At a sufficiently negative potential, benzene is the only product of a four-electron reduction of the diphenyliodonium cation. Wave Ia for a diphenyliodonium halide is attributed to reduction of the phenyl mercuric halide resulting from reaction of starting material with mercury, whereas wave Ib is caused by reduction of solution-soluble diphenyliodonium cations. Wave II arises from reduction of iodobenzene (a product formed by processes associated with the appearance of waves Ia and Ib), and wave III is due to reduction of adsorbed phenylmercury radicals (the other species formed by reactions responsible for waves Ia and Ib). These conclusions have been substantiated by independent pulse polarographic, cyclic voltammetric, and coulometric studies of phenyl mercuric halides.

Mechanistic investigation of the copper-catalyzed reactions of diphenyliodonium salts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMechanistic investigation of the copper-catalyzed reactions of diphenyliodonium saltsThomas P. LockhartCite this: J. Am. Chem. Soc. 1983, 105, 7, 1940–1946Publication Date (Print):April 1, 1983Publication History Published online1 May 2002Published inissue 1 April 1983https://doi.org/10.1021/ja00345a045RIGHTS & PERMISSIONSArticle Views1527Altmetric-Citations78LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (915 KB) Get e-Alerts Get e-Alerts

Specific influence of the electrode material in the electrochemical reduction of diphenyliodonium salts

During the study of the influence of the electrode material on the electrochemical reduction of phenylonium salts, we found that borofluoride and halides of diphenyliodonlum, in contrast to phenylonium salts of elements of groups V and VI, are reduced on Hg but not on Pt electrode [reduction waves were not observed in acetonitrile up to --1.8 V with reference to saturated calomel electrode (SCE)]. In the literature there are no data available on the reduction of arylonium salts on Pt, and we therefore studied the reduction of several onium salts (Ph~Bi+BF~ -, Ph~Sb+X -, PhsS+X -, where X= BF~-, C1-, Br-, I-) on the rotating Pt electrode in acetonitrile. It was found that all the above salts are reduced on Pt, and their polarograms are similar to those of the reduction of these salts on Hg with a certain shift of E111.

ChemInform Abstract: Σ‐ARYL COMPLEXES OF IRIDIUM‐ DIPHENYLIODONIUM SALTS AS PHENYLATING AGENTS IN TRANSITION METAL CHEMISTRY

AbstractDie Diphenyljodonium‐Salze (II) und (IV) reagieren mit den Ir(I)‐Komplexen (III) unter Bildung der o‐Phenyl‐Ir(III)‐Komplexe (I) bzw. der vermutlich dimeren Salze (V) (Ausbeuten 55‐60%).

σ-Aryl complexes of iridium: diphenyliodonium salts as phenylating agents in transition metal chemistry

Diphenyliodonium salts readily react with [IrX(CO)(PR3)2] (X = Cl, Br; PR3 = PPh3 or PMePh2) to yield iridium(III) σ-phenyl complexes of general composition [IrXY(C6H5)(CO)(PR3)2] (Y = Cl, BF4). The possible structures of these compounds, and their occurrence in the decomposition of iridium aryldiazenato complexes, are discussed.

The synthesis of halogenated diphenyliodonium salts and their coupling products with halogenated phenols

The synthesis of halogenated diphenyliodonium salts and their coupling products with halogenated phenols

The reaction between triethyl phosphite and diphenyliodonium salts. Formation of diethyl phenylphosphonate and 1,4-diiodobenzene.

The reaction between triethyl phosphite and diphenyliodonium salts. Formation of diethyl phenylphosphonate and 1,4-diiodobenzene.

Photolysis of diphenyliodonium salts in alcohol solutions

Photolysis of diphenyliodonium salts in alcohol solutions

Identification of some polyatomic inorganic anions as their diphenyliodonium salts by infrared spectroscopy and interpretation of the spectra

The main features of infrared spectra of the diphenyliodonium salts of some polyatomic anions are reported and interpreted, and their application in qualitative analysis discussed.

Influence of the identical anion on the reaction between diphenyliodonium salts and metalic mercury

Influence of the identical anion on the reaction between diphenyliodonium salts and metalic mercury

Decomposition of diphenyliodonium salts in the presence of aniline

Decomposition of diphenyliodonium salts in the presence of aniline

Degree of dissociation of diphenyliodonium salts in water and methanol

Degree of dissociation of diphenyliodonium salts in water and methanol