- Reaction of PbO2 with Solutions of Methylbenzonitriles
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The yield of products formed by low-temperature oxidation of methylbenzonitriles with PbO2 in fluorosulfonic acid solutions was studied in relation to the stabilization factor of the reaction system. The revealed correlation is common for methylbenzonitriles differing in the degree of alkylation and in the oxidation mechanism.
- Kol'tsov,Salfetnikova
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- Silver-Catalyzed C(sp3)-H Chlorination
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A silver-catalyzed chlorination of benzylic, tertiary, and secondary C(sp3)-H bonds was developed. The reaction proceeded with as low as 0.2 mol % catalyst loading at room temperature under air atmosphere with synthetically useful functional group compatibility. The regioselectivity and reactivity tendencies suggest that the chlorination proceeded through a radical pathway, but an intermediate alkylsilver species cannot be ruled out.
- Ozawa, Jun,Kanai, Motomu
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supporting information
p. 1430 - 1433
(2017/03/23)
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- Oxidation of Aromatic Compounds. V. Oxidation of Substituted Benzonitriles and 2,4,6-Triaryl-1,3,5-Triazines in System HSO3F-PbO2
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Low-temperature oxidation of substituted benzonitriles by the system HSO3F-PbO2 proceeds with intermediate formation of cation-radicals and leads to substitution of hydrogen atoms of the methyl group or benzene ring. This reaction provides a route for preparation of chloromethylsubstituted benzonitriles, diarylmethanes, diaryls, arylfluorosulfonates and substituted benzamides with cyano groups. In the case of methyl derivatives of 2,4,6-triphenyl-1,3,5-triazine substitution of the first and then the second hydrogen atom of the same methyl group transforms it into hydroxy or chloromethyl group, or into the aldehyde function.
- Rudenko,Salfetnikova,Vasil'ev
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p. 1447 - 1470
(2007/10/03)
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- THE ESR SPECTRA, STRUCTURE, AND REACTIVITY OF AROMATIC RADICAL-CATIONS IN SUPERACIDS
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The oxidation of aromatic compounds by lead dioxide in superacids based on fluorosulfonic acid at -75 deg C takes place by a one-electron mechanism and leads in many cases to relatively stable radical-cations.The ESR spectra, the isotropic hyperfine coupling constants, data on the reactivity of the radical-cations, and the structures of the final products from their transformations under "long-life" conditions are presented.
- Rudenko, A. P.
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p. 1946 - 1980
(2007/10/03)
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