<b>Carbonium Ion Salts. III. Spectra and Decomposition of Tropenium Halides in Methylene Chloride</b>

Harmon, Kenneth M.; Cummings, Frank E.; Davis, Dick A.; Diestler, Dennis J.

doi:10.1021/ja00860a035

Cited by 23 publications

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“…The extensive work on pyridinium iodides has provided a comprehensive example of IPCT between aromatic cations and iodide. Other aromatic cations such as pyrylium, 416 transstyrylpyridinium, 417 and tropylium 418,419 have also been shown to undergo IPCT with halides. For example, the chloride, bromide, and iodide salts of tropylium have been synthesized and studied.…”

Section: Halide-to-acceptor Charge Transfermentioning

confidence: 99%

“…In CH 2 Cl 2 , the charge-transfer band shifted to higher energy as the halide became harder to oxidize. 418 Subsequent work utilized tropylium and iodide as ligands for a molybdenum complexes, as shown in Figure 32. 420 Significantly, the authors observed a low energy absorption (735 nm) that was assigned to a ligand-to-ligand charge transfer.…”

Section: Halide-to-acceptor Charge Transfermentioning

confidence: 99%

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Halide Photoredox Chemistry

et al. 2019

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Halide photoredox chemistry is of both practical and fundamental interest. Practical applications have largely focused on solar energy conversion with hydrogen gas, through HX splitting, and electrical power generation, in regenerative photoelectrochemical and photovoltaic cells. On a more fundamental level, halide photoredox chemistry provides a unique means to generate and characterize one electron transfer chemistry that is intimately coupled with X−X bond-breaking and -forming reactivity. This review aims to deliver a background on the solution chemistry of I, Br, and Cl that enables readers to understand and utilize the most recent advances in halide photoredox chemistry research. These include reactions initiated through outer-sphere, halide-to-metal, and metal-toligand charge-transfer excited states. Kosower's salt, 1-methylpyridinium iodide, provides an early outer-sphere charge-transfer excited state that reports on solvent polarity. A plethora of new inner-sphere complexes based on transition and main group metal halide complexes that show promise for HX splitting are described. Long-lived charge-transfer excited states that undergo redox reactions with one or more halogen species are detailed. The review concludes with some key goals for future research that promise to direct the field of halide photoredox chemistry to even greater heights. CONTENTS 1. Introduction, Background, and Motivation

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Section: Halide-to-acceptor Charge Transfermentioning

confidence: 99%

Section: Halide-to-acceptor Charge Transfermentioning

confidence: 99%

Halide Photoredox Chemistry

et al. 2019

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The 2,1‐benzisothiazolo[2,3‐b]‐2,1‐benzisothiazole system, synthesis and properties

McKinnon

Duncan

1988

Journal of Heterocyclic Chem

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Katalysierte Homologisierung von Benzol mit Diazomethan zum Cycloheptatrien

Müller

Fricke

1963

Justus Liebigs Ann. Chem.

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Zur Darstellung von Cycloheptatrien 2 ) haben MEERWEIN sowie VON E. DOERING Benzol rnit Diazomethan photochernisch urngesetzt3).Wir erhielten bei dieser Photo-Synthese bis zu 75% Cycloheptatrien, aber auch stets im Gemisch mit Toluol und basischen Beiprodukten4). Ausgehend von der Annahme, daO die Bildung des Toluols auf den hohen Energieinhalts) des bei der Photolyse entstehenden freien Carbens lCH2 zuruckzufiihren ist, zielten unsere Untersuchungen darauf hin, ein ,,desaktiviertes" Carben von geringerem Energieinhalt zu erzeugen. Uber eine ahnliche ,,Desaktivierung" des Carbens berichteten SIMMONS und SMiTH6) sowie WIITIG und SCHWARZENBACH~), denen mit dem lntermediarkomplex aus Methylenjodid und einem Zink-Kupfer-Paar einerseits bzw. dem Reaktionsprodukt aus Diazomethan und Zinkjodid andererseits die stereospezifische, selektive Cyclopropanisierung olefinischer Doppelbindungen gelungen ist. Ein Versuch iiberzeugte uns jedoch davon, da8 diese Intermediarkomplexe fur die Ringerweiterung des Benzols nicht geeignet sind.

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Carbonium Ion Salts. III. Spectra and Decomposition of Tropenium Halides in Methylene Chloride

Cited by 23 publications

References 1 publication

Halide Photoredox Chemistry

Halide Photoredox Chemistry

The 2,1‐benzisothiazolo[2,3‐b]‐2,1‐benzisothiazole system, synthesis and properties

Katalysierte Homologisierung von Benzol mit Diazomethan zum Cycloheptatrien

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