<b>Directive Effects in the Attack of Phenyl Radicals on Carbon-Hydrogen Bonds</b>

Bridger, Robert F.; Russell, Glen A.

doi:10.1021/ja00906a009

Cited by 178 publications

(77 citation statements)

References 4 publications

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“…The last named product may arise by dehydration of I, I-diphenylethanol (formed by hydrogen abstraction by the ethoxy radical) or perhaps by a concerted decomposition of the peroxide which does not involve free radicals dilute solution in CCI,. The attack of phenyl radical on CCl,, reaction [12] is extremely rapid (14) and reaction [ I l l would lead to the production of chlorobenzene. Our results are consistent with the reactions given in Scheme I.…”

mentioning

confidence: 99%

Absolute rate constants for hydrocarbon autoxidation. XV. The induced decomposition of some t-hydroperoxides

Howard¹,

Ingold²

1969

Can. J. Chem.

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The radical induced decomposition of several t-hydroperoxides at 30' has been studied. In the self reaction of t-alkylperoxy radicals the ratio of the rates of alkoxy radical diffusion from the cage to combination in the cage is essentially independent of the size of the t-alkyl group.The rate constant for abstraction from hydroperoxides of the hydroperoxidic hydrogen by alkoxy radicals is about 4 x lo6 M-'s-' at 30". This reaction has a deuterium isotope effect, k,/k, 2 5.The 1,l-diphenylethoxy radical undergoes a 1,2-phenyl shift to yield the I-phenyl-I-phenoxyethyl radical more rapidly that it undergoes !3-scission.

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confidence: 99%

Absolute rate constants for hydrocarbon autoxidation. XV. The induced decomposition of some t-hydroperoxides

Howard¹,

Ingold²

1969

Can. J. Chem.

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“…The first systematic investigation of the abstraction reactions of the phenyl radical was carried out by Russell and Bridger (2)(3)(4). Most studies with phenyl radicals have dealt with homolytic arylation (5~19) although other workers have also done some investigations on the abstraction reactions of the phenyl radical (6,14,(19)(20)(21)(22)(23)(24)(25) .…”

Section: Literature Reviewmentioning

confidence: 99%

“…Thermal decomposition of benzoyl peroxide not only gives benzene but also benzoic ac!id and com plicated products. Bridger (2)(3)(4) has shown that PA,T is the most ideal generator of phenyl radicals.…”

Section: Literature Reviewmentioning

confidence: 99%

“…Three assumptions involved in the derivation of equation The decomposition of PAT in pure carbon tetrachloride has been shown to always yield some benzene (2,4). The benzene has "been ascribed to a cage reaction.…”

Section: Literature Reviewmentioning

confidence: 99%

“…That this yield of benzene can be used as a correction factor has been justified by Bridger (2)(3)(4) in the fact that the yield of benzene did not significantly increase when the solvent was changed to pure chlorobenzene from carbon tetrachloride or when mixtures of carbon tetrachloride with diphenyl ether, biphenyl or triphenylamine were used.…”

Section: Literature Reviewmentioning

confidence: 99%

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The reactivity of phenyl radicals in abstraction reactions toward some heteroaromatic compounds

Schoeb

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Kinetics of C6H5 radical reactions with 2-methylpropane, 2,3-dimethylbutane and 2,3,4-trimethylpentane

Park

Gheyas

Lin

1999

Int. J. Chem. Kinet.

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The absolute bimolecular rate constants for the reactions of C 6 H 5 with 2-methylpropane, 2,3-dimethylbutane and 2,3,4-trimethylpentane have been measured by cavity ringdown spectrometry at temperatures between 290 and 500 K. For 2-methylpropane, additional measurements were performed with the pulsed laser photolysis/mass spectrometry, extending the temperature range to 972 K. The reactions were found to be dominated by the abstraction of a tertiary C-H bond from the molecular reactant, resulting in the production of a tertiary alkyl radical:

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Directive Effects in the Attack of Phenyl Radicals on Carbon-Hydrogen Bonds

Cited by 178 publications

References 4 publications

Absolute rate constants for hydrocarbon autoxidation. XV. The induced decomposition of some t-hydroperoxides

Absolute rate constants for hydrocarbon autoxidation. XV. The induced decomposition of some t-hydroperoxides

The reactivity of phenyl radicals in abstraction reactions toward some heteroaromatic compounds

Kinetics of C6H5 radical reactions with 2-methylpropane, 2,3-dimethylbutane and 2,3,4-trimethylpentane

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