The Relative Reactivities of the Seven Nuclear Positions of Isoquinoline to Free-Radical Phenylation

1979 ◽  
Vol 32 (2) ◽  
pp. 345 ◽  
Author(s):  
LK Dyall ◽  
CJ Pullin
Keyword(s):  
Free Radical ◽  
Theoretical Predictions ◽  
Radical Phenylation ◽  
Reactivity Order

Free-radical phenylation of isoquinoline has been effected both by photolysis of phenylthallium(III) di(trifluoroacetate) and by the action of pentyl nitrite on aniline. Analysis of the isomeric phenyl isoquinoline mixture by g.l.c. and h.p.l.c. established the reactivity order in the isoquinoline nucleus to be 1 > 5 > 8 > 4 > 3,6,7. This experimental order is compared with the eight published theoretical predictions, none of which is correct.

scholarly journals The free-radical phenylation of isoquinolinium cation

1982 ◽  
Vol 35 (10) ◽  
pp. 2179 ◽  
Author(s):  
AJ Beveridge ◽  
LK Dyall
Keyword(s):  
Free Radical ◽  
Acid Solution ◽  
Trifluoroacetic Acid ◽  
Theoretical Predictions ◽  
Radical Phenylation

Free-radical phenylation of isoquinolinium cation has been effected by photolysis of phenylthalliurn(III)di(trifluoroacetate) in a trifluoroacetic acid solution of isoquinoline. Analysis (g.l.c. and h.p.l.c.) of the isomeric phenylisoquinoline mixture showed that the dominant product (81.1 %) was 1-phenylisoquinoline, in accordance with two published theoretical predictions.

scholarly journals Solvent Effect on the Free Radical Phenylation with Phenylazotriphenylmethane

1973 ◽  
Vol 46 (2) ◽  
pp. 546-550 ◽  
Author(s):  
Michio Kobayashi ◽  
Hiroshi Minato ◽  
Nobuko Watanabe
Keyword(s):  
Free Radical ◽  
Solvent Effect ◽  
Radical Phenylation

Free-Radical Phenylation of Ferricenium Ion

1964 ◽  
Vol 86 (5) ◽  
pp. 952-953 ◽  
Author(s):  
A. L. J. Beckwith ◽  
R. J. Leydon
Keyword(s):  
Free Radical ◽  
Radical Phenylation

The Free Radical Phenylation of 2,4-Dinitrotritiobenzene1

1957 ◽  
Vol 79 (11) ◽  
pp. 2941-2942 ◽  
Author(s):  
Charles C. Price ◽  
Robert J. Convery
Keyword(s):  
Free Radical ◽  
Radical Phenylation

REACTIONS OF PHENYL-SUBSTITUTED HETEROCYCLIC COMPOUNDS: III. FREE-RADICAL PHENYLATION OF 1-PHENYLPYRAZOLE

1963 ◽  
Vol 41 (8) ◽  
pp. 2086-2094 ◽  
Author(s):  
Brian M. Lynch ◽  
Misbahul Ain Khan
Keyword(s):  
Free Radical ◽  
Benzoyl Peroxide ◽  
Phenyl Ring ◽  
Heterocyclic Compounds ◽  
Pyrazole Ring ◽  
Free Valence ◽  
Resonance Theory ◽  
Phenyl Radicals ◽  
Radical Phenylation

Phenyl radicals furnished by benzoyl peroxide attack both rings of 1-phenylpyrazole, and the orientation of substitution has been examined using gas–liquid partition chromatography.Substitution occurs at all positions of the phenyl ring, although predominantly at the ortho positions, while attack in the pyrazole ring is confined to the 3-position. The results are in agreement with the suggestion that the free valence at a given position is a major factor in determining the orientation of free-radical phenylation of 1-phenylpyrazole, but in conflict with predictions from resonance theory.

Further Data on the Free Radical Phenylation of 2,4-Dinitrotritiobenzene

1958 ◽  
Vol 80 (15) ◽  
pp. 4101-4101 ◽  
Author(s):  
Robert J. Convery ◽  
Charles C. Price
Keyword(s):  
Free Radical ◽  
Radical Phenylation
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