Halogen abstraction studies. VI. Abstraction of bromine by phenyl radicals from C3-C8 cycloalkyl mono- and trans-1,2-dibromides

Danen, Wayne C.; Rose, Kenneth A.

doi:10.1021/jo00893a016

Cited by 11 publications

(1 citation statement)

References 6 publications

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“…The development of synthetic strategies based on XAT processes has been largely impacted by understanding the factors which govern this radical reactivity . Fundamental work from Ingold, − Danen, ,,,, Lorand, Scaiano, Lusztyk, Newcomb, Curran, , Chatgilialoglu, , Giese, Crich and Galli has provided extensive knowledge in this respect and many absolute rate constants have been determined. While a detailed discussion of these mechanistic experiments is beyond the scope of the review, a summary of the rate constants for commonly used XAT reagents and alkyl/aryl halides is presented in Table .…”

Section: Mechanistic Aspects Of Xat Reactivitymentioning

confidence: 99%

Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis

Hernández¹,

Constantin²,

2021

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The halogen-atom transfer (XAT) is one of the most important and applied processes for the generation of carbon radicals in synthetic chemistry. In this review, we summarize and highlight the most important aspects associated with XAT and the impact it has had on photochemistry and photocatalysis. The organization of the material starts with the analysis of the most important mechanistic aspects and then follows a subdivision based on the nature of the reagents used in the halogen abstraction. This review aims to provide a general overview of the fundamental concepts and main agents involved in XAT processes with the objective of offering a tool to understand and facilitate the development of new synthetic radical strategies.

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Section: Mechanistic Aspects Of Xat Reactivitymentioning

confidence: 99%

Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis

Hernández¹,

Constantin²,

2021

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Thermolabile Kohlenwasserstoffe, II: Der Einfluß der Ringgröße auf die Thermolyse von 1,1′‐Diphenyl,1′‐bicycloalkylen

1976

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1,l'-Diphenyl-1,l'-bicycloalkyle 1 mit der RinggroBe n = 3-8 wurden synthetisiert und die Geschwindigkeiten der Thermolyse bestimmt. Die RinggroDe hat einen ungewohnlich grol3en EinfluD auf die Zerfallskonstanten (Faktor 1014 zwischen 1 n = 3 und n = 8 bei 220"C), der nicht allein durch unterschiedlichen I-strain gedeutet werden kann. Mit der RinggroDe zunehmende abstoDende Wechselwirkungen im Bereich der van-der-Waals-Radien nicht miteinander verbundener Gruppen von der Art des Front-strains werden aus Modellbetrachtungen und dem Vergleich mit den Thermolysekonstanten der 1,l'-Diphenyl-azocycloalkane 6 fur den Hauptteil der sterischen Beschleunigung verantwortlich gemacht. Thermolabile Hydrocarbons, 11')Ring Size Effects on the Rates of Thermolysis of l,l'-Diphwyl-l,l'-bicycloalkylsz~ 1,l'-Diphenyl-1,l'-bicycloalkyls 1 with the ring size n = 3-8 were prepared and their rates of thermal decomposition were determined. An unprecedented large ring size effect on the rates (factor 1014 for 1 n = 3 and n = 8 at 220°C) was observed. In addition to I-strain effects steric repulsions of non-bonded groups, like F-strain, are made responsible for the main part of the ring size effect according to models and by comparison with the ring size effect on the thermal decomposition of I, Ildiphenyl-azocycloalkanes 6.Die unterschiedliche Bildungstendenz verschieden strukturierter Alkyl-Radikale ist ein fur die Radikalchemie wichtiges und daher vie1 diskutiertes Phanomen 3-6). In jungerer Zeit erkannte man, daB es dabei nicht eine, allein von der thermodynamischen Stabilitat der Alkyl-Radikale abhangige Reaktivitatsreihe gibt, sondern daD Grundzustandseffekte 3.4*6) und polare Effekte 3, von Reaktion zu Reaktion einen unterschiedlichen EinfluB auf die Radikalbildungsgeschwindigkeit

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ChemInform Abstract: HALOGEN ABSTRACTION STUDIES PART 6, ABSTRACTION OF BROMINE BY PHENYL RADICALS FROM C3‐C8 CYCLOALKYL MONO‐ AND TRANS‐1,2‐DIBROMIDES

Danen¹,

Rose²

1975

Chemischer Informationsdienst

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Halogen abstraction studies. VI. Abstraction of bromine by phenyl radicals from C3-C8 cycloalkyl mono- and trans-1,2-dibromides

Cited by 11 publications

References 6 publications

Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis

Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis

Thermolabile Kohlenwasserstoffe, II: Der Einfluß der Ringgröße auf die Thermolyse von 1,1′‐Diphenyl,1′‐bicycloalkylen

ChemInform Abstract: HALOGEN ABSTRACTION STUDIES PART 6, ABSTRACTION OF BROMINE BY PHENYL RADICALS FROM C3‐C8 CYCLOALKYL MONO‐ AND TRANS‐1,2‐DIBROMIDES

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