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

1983 ◽  
Vol 36 (5) ◽  
pp. 1031 ◽  
Author(s):  
TJ Broxton ◽  
MJ Mcleish

A comparison of the relative amounts of dediazoniation, SNAr and aryne reactions of 4-chloro-3- nitrobenzenediazonium ion with methoxide ion in CH3OH and in CD3OH confirms that the dediazoniation reaction involves hydride abstraction from the alkoxide ion by the electrophilic terminal nitrogen atom of the diazonium ion. Furthermore, the relative amounts of anionic and free-radical dediazoniation are the same in CH3OH and in CD3OH. This confirms that the partitioning between the free-radical and anionic pathways for dediazoniation is on the aryl diimide and not on the free diazonium ion. Some previously reported results on the solvent effect (methanol against ethanol) for the reaction have been reinterpreted in the light of the above conclusions.


1982 ◽  
Vol 35 (10) ◽  
pp. 2179 ◽  
Author(s):  
AJ Beveridge ◽  
LK Dyall

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.


1979 ◽  
Vol 32 (2) ◽  
pp. 345 ◽  
Author(s):  
LK Dyall ◽  
CJ Pullin

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.


1999 ◽  
Vol 103 (25) ◽  
pp. 4893-4909 ◽  
Author(s):  
Yao-Yuan Chuang ◽  
Mala L. Radhakrishnan ◽  
Patton L. Fast ◽  
Christopher J. Cramer ◽  
Donald G. Truhlar

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