2015
DOI: 10.1016/j.jfluchem.2015.08.016
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2-(Fluoro-) and 2-(methoxyanilino)-1,4-naphthoquinones. Synthesis and mechanism and effect of fluorine substitution on redox reactivity and NMR

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Cited by 15 publications
(7 citation statements)
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“…Successful results on the use of the Ce(III) catalyst in the oxidative amination reaction of quinones with arylamines have been reported in literature [ 32 38 ]. These acid catalysts probably increase the electrophilic character of the enone system of the quinones, via coordination with the oxygen atom of the carbonyl group, thus promoting the Michael-type addition [ 35 , 39 , 40 ].…”
Section: Resultsmentioning
confidence: 99%
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“…Successful results on the use of the Ce(III) catalyst in the oxidative amination reaction of quinones with arylamines have been reported in literature [ 32 38 ]. These acid catalysts probably increase the electrophilic character of the enone system of the quinones, via coordination with the oxygen atom of the carbonyl group, thus promoting the Michael-type addition [ 35 , 39 , 40 ].…”
Section: Resultsmentioning
confidence: 99%
“…The acid-induced formation of the arylation compounds 16-28 from acylquinones 9-15 and their reaction with N , N -dimethylaniline are proposed to occur according to the mechanism of reaction depicted in Scheme 3 . This approach is based on the reaction mechanism for the Ce(III)-promoted phenylamination reaction of 1,4-naphthoquinone with 2-fluoro- and 2-methoxyanilines reported by Leyva et al [ 35 ]. Initially, a selective conjugate Michael-type addition of the arylamine across the enone system C 3 =C 2 -C 1 =O seems plausible.…”
Section: Resultsmentioning
confidence: 99%
“…The aromatic proton H(5) takes part intermolecular C–H···O interaction ( Table 2 ) in most of the crystal structures of known derivatives; if such interactions exist in the solution, the chemical shift variation is expected. The 1 H chemical shift was observed at ~ δ = 7.8–7.9 ppm in all compounds; this implies that the intermolecular C–H···O interaction does not directly affect its chemical shift [ 45 ]. A similar inference for the 1 H chemical shift of other benzenoid ring protons H(8), H(6), and H(7) can be drawn.…”
Section: Resultsmentioning
confidence: 99%
“…It is not possible to separate the ortho and para isomers. The substituted naphthoquinones were prepared by the method reported in the literature with several modifications [40,41].…”
Section: Synthesizedmentioning
confidence: 99%