Organic and Inorganic Chemistry of Iodine Oxides

Masson, Irvine

doi:10.1038/139150a0

Cited by 11 publications

(7 citation statements)

References 2 publications

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“…Early work in this field was done by Masson and coworkers, who discovered that arenes could be treated with iodic acid or iodosyl sulfate to form diaryliodonium salts. [42] This theme was further developed by Beringer, who also performed anion exchanges to generate the corresponding diaryliodonium halides (Scheme 6 a). [13,14] A modified procedure has recently been published (see Section 2.5).…”

Section: Synthesis With Preformed Inorganic Hypervalent Iodine Reagentsmentioning

confidence: 99%

Diaryliodonium Salts: A Journey from Obscurity to Fame

2009

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The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent of novel, facile, and efficient synthetic routes to these compounds, many more applications can be foreseen. Herein we provide an overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts.

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Section: Synthesis With Preformed Inorganic Hypervalent Iodine Reagentsmentioning

confidence: 99%

Diaryliodonium Salts: A Journey from Obscurity to Fame

2009

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“…[37] Die erste Synthese von chiralen Diaryliodoniumsalzen wurde 1999 von Ochiai und Mitarbeitern veröffentlicht. [38] 2-(Diacetoxyiod)-1,1'-binaphthyl [39] [42] Die Methode wurde durch Beringer weiterentwickelt, der auch Anionenaustausche zur Bildung der entsprechenden Diaryliodoniumhalogenide vornahm (Schema 6 a). [13,14] Eine modifizierte Prozedur wurde erst unlängst veröffentlicht (siehe Abschnitt 2.5).…”

Section: Strategien Zur Synthese Von Diaryliodoniumsalzenunclassified

“…Frühe Arbeiten auf diesem Gebiet gehen auf Masson und Mitarbeiter zurück, die entdeckten, dass Arene mit Iodsäure oder Iodosylsulfat zu Diaryliodoniumsalzen umgesetzt werden können. [42] Die Methode wurde durch Beringer weiterentwickelt, der auch Anionenaustausche zur Bildung der entsprechenden Diaryliodoniumhalogenide vornahm (Schema 6 a). [13,14] Eine modifizierte Prozedur wurde erst unlängst veröffentlicht (siehe Abschnitt 2.5).…”

Section: Synthesen Mit Präformierten Organischen Iod(iii)-verbindungenunclassified

Diaryliodoniumsalze – aus dem Nichts ins Rampenlicht

2009

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Die jüngsten bahnbrechenden Entwicklungen bei der Anwendung von Diaryliodoniumsalzen in Kreuzkupplungsreaktionen haben diese ehemals unterentwickelte Klasse von Reagentien in die vorderste Reihe der organischen Chemie katapultiert. Mit dem Aufkommen neuartiger, einfacher, effizienter Methoden zur Synthese dieser Reagentien lassen sich noch sehr viel mehr Einsatzmöglichkeiten voraussehen. Wir bieten hier einen Überblick über die historischen und neuerlichen Fortschritte bei der Synthese und Anwendung von Diaryliodoniumsalzen.

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“…Preparation: trans-(I) and cis-dichlorocycloheplane (11) [Z], trans-(111) and cis-dichlorocyclooctane (IV) [3], exo, exo-2,3-dichloro-exo, exo-~.6-dimcthoxycrsrbonyl-b~cyclo~l .2.Zlheptane [4] [5], trans-9,lO-dichZoro-decalin (XX) [5], d. 1-7.2-dichlorosuccinic anhydride (XIV) [6], trans-and cis-7,2-dichlorohenzocyclohutelze (XV & XVI) [7], trans-and cis-7,2-dichZoroacenaphthene (XVII & XVIII) [S] were prepared by previously published methods, meso dichlorosuccinic acid (VIII) was a commercial product and the d.Z acid (XII) was prepared from XIV by hydrolysis.…”

Section: Nuclear Quadrupole Resonance and Stereochemistry 11 Vicinalmentioning

confidence: 99%

“…In this paper we report the 35Cl NQR frequencies of a number of 1,Zdichloro derivatives of carbocyclic systems of known configuration and in the light of these and of other previously reported results, attempt to estimate the magnitude of such an effect.Experimental. Instrumentation, see [l].Preparation: trans-(I) and cis-dichlorocycloheplane (11) [Z], trans-(111) and cis-dichlorocyclooctane (IV) [3], exo, exo-2,3-dichloro-exo, exo-~.6-dimcthoxycrsrbonyl-b~cyclo~l .2.Zlheptane [4] (V), exo, endo-2,3-dichloro-exo, exo-5,6-dimethoxycarhonyl-bicyclo[7 .Z.Z]heptane (VI), [4], exo, exo-2,3dichloro- endo, endo-5,6-dimethoxycarbonyl-bicyclo[7.r?.2]keptane (VII) [4], exo, exo-2,3-dichloro- endo, endo-5,6-dicurboxy-bicyclo[l.2.2]keptane (VIII) [4], exo, exo-2, 3-dichloro-bicyclo[7.2.2]heptane (IX), exo, exo-3, 5-dichZ0ro-tricycZo[2.2.7.0~~~]heptane (XIV) [5], trans-9,lO-dichZoro-decalin (XX) [5], d. 1-7.2-dichlorosuccinic anhydride (XIV) [6], trans-and cis-7,2-dichlorohenzocyclohutelze (XV & XVI) [7], trans-and cis-7,2-dichZoroacenaphthene (XVII & XVIII ) [S] were prepared by previously published methods, meso dichlorosuccinic acid (VIII) was a commercial product and the d.Z acid (XII) was prepared from XIV by hydrolysis.We thank Dr. C . A .…”

mentioning

confidence: 99%

ChemInform Abstract: NUCLEAR QUADRUPOLE RESONANCE AND STEREOCHEMISTRY PART 2, VICINAL CIS‐ AND TRANS‐DICHLORO DERIVATIVES OF CARBOCYCLIC SYSTEMS

Ardalan¹,

Lücken²,

Masson³

1973

Chemischer Informationsdienst

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Summary. The 36Cl quadrupole resonance frequencies of sets of isomeric vicinal dichloro derivatives of carbocyclic molecules are presented. In all cases except one -cis-and trans-l,Z-dichloro-acenaphthene -the configuration has only a small effect on the resonance frequency. This implies that the frequency-differences in cyclic a-chloroethers reported in Part I of this series [l]are indeed due to a specific interaction with the oxygen atom. The difference between the acenaphthenes may be due t o hyperconjugation between the C-Cl bond and the aromatic system.In the first paper in this series [l] it was shown that the 35Cl NQR frequency of cyclic a-chloro ethers depends very markedly on the configuration, (axial or equatorial) of the carbon-chlorine bond. Most of the compounds whose quadrupole resonance spectra were reported therein contained either vicinal dichloro groups or a polar substituent in a vicinal position with respect t o the nucleus under study so that at least a part of the effects reported in [l] could arise from the relative positions of the two vicinal groups. In this paper we report the 35Cl NQR frequencies of a number of 1,Zdichloro derivatives of carbocyclic systems of known configuration and in the light of these and of other previously reported results, attempt to estimate the magnitude of such an effect.Experimental. Instrumentation, see [l]. We thank Dr. C . A . de Meij for kindly supplying the le, Z e , 3e, 4e, 5e, 6e-hexachlorophenylcyclohexane (X) [9] and l a , Za, 3e, 4e, 5e, 6e-hexachlorophenylcyclohexane (XI) [9] and Dr. Kalvoda of CIBA-GEIGY, Base1 for the four steroids: 3~-acetoxy-5,6~-dichZoro-5cc-androstune-17-m e (XXI), 3~-acetoxy-5-chloro-6~-hydvoxy-5~-undrostane-77-one (XXII), 3~-acetoxy-5-ckloro-6p, 19-epoxy-5sc-androstane-77-one (XXIII) and 6cc-chloro-4-ene-androstane-3,~7-d~one (XXIV). Preparation: trans-(I) and cis-dichlorocycloheplane (11)[

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Organic and Inorganic Chemistry of Iodine Oxides

Cited by 11 publications

References 2 publications

Diaryliodonium Salts: A Journey from Obscurity to Fame

Diaryliodonium Salts: A Journey from Obscurity to Fame

Diaryliodoniumsalze – aus dem Nichts ins Rampenlicht

ChemInform Abstract: NUCLEAR QUADRUPOLE RESONANCE AND STEREOCHEMISTRY PART 2, VICINAL CIS‐ AND TRANS‐DICHLORO DERIVATIVES OF CARBOCYCLIC SYSTEMS

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