Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Aromatic Arylation with Aryl Radicals. IV. The Kinetic Hydrogen Isotope Effect in the Aromatic Phenylation with Phenyl Radical
Nobumasa KamigataHiroshi MinatoMichio Kobayashi
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1972 Volume 45 Issue 7 Pages 2042-2046

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Abstract

Anisole-4d, chlorobenzene-4d, chlorobenzene-d5, nitrobenzene-d5, m-dinitrobenzene-d4, and 1,3,5-tri-t-butylbenzene-d3 were phenylated with phenyl radical generated from PhN2BF4–NaNO2, N-nitrosoacetanilide or phenylazotriphenylmethane(PAT), and the isotope effect in these phenylations was determined. The values of kHkD in the phenylations of chlorobenzene and 1,3,5-tri-t-butylbenzene are not so larger than unity, whereas that in the phenylation at the 2-position of m-dinitrobenzene with PAT was very large (∼11).

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