102607-12-5Relevant articles and documents
OXIDATION BY THE SALTS OF METALS. VII. PLUMBATION AND OXIDATIVE SUBSTITUTION OF AROMATIC COMPOUNDS IN THE LEAD TETRAACETATE-LITHIUM CHLORIDE SYSTEM IN THE PRESENCE OF PERFLUORINATED CARBOXYLIC ACIDS
Serguchev, Yu. A.,Davydova, V. G.,Makhon'kov, D. I.,Beletskaya, I. P.
, p. 1006 - 1011 (2007/10/02)
The oxidation of benzene and substituted benzenes PhX with electron-donating (X = CH3, OCH3) and electron-withdrawing (X = Hlg, CF3, NO2) substituents in the Pb(OAc)4-LiCl system was investigated in the presence of perfluorinated carboxylic acids RfCOOH (Rf = CF3, C6F13).The reaction leads to the plumbation, chlorination, and acyloxylation products.It was shown that the reactions take place through the formation of aryl derivatives of lead(IV) with the participation of mixed-ligand complexes of lead.The products from the plumbation of toluene (in C6F13COOH in the absence of lithium chloride) and benzotrifluoro were isolated.In trifluoroacetic acid these intermediates undergo intramolecular redox decomposition with ligand transfer.The halogenobenzenes and benzotrifluoride are oxidized selectively in the CF3COOH-Pb(IV)-LiCl system, giving the corresponding aryl chlorides with yields close to quantitative (80-90percent).
OXIDATION OF AROMATIC COMPOUNDS WITH LEAD TETRAACETATE IN THE PRESENCE OF PERFLUORINATED CARBOXYLIC ACIDS AND LITHIUM CHLORIDE
Serguchev, Yu. A.,Davydova, V. G.,Stetsyuk, G. A.,Blendonogii, D. P.,Beletskaya, I. P.
, p. 726 - 730 (2007/10/02)
The oxidation of aromatic compounds (chlorobenzene, benzene, and toluene) with lead tetraacetate in the presence of perfluorinated carboxylic acids and lithium chloride in a hydrocarbon medium was investigated.The main compounds obtained during oxidation in the presence of lithium chloride are products from chlorination in the ring, while those in the absence of lithium chloride are aryl perfluoroalkanecarboxylates.The high yield of the chlorine-substituted compounds and aryl perfluoroalkanecarboxylates with a specific ratio of the components in the oxidizing system presupposes the formation of organolead compounds with the appropriate ligand composition at the intermediate stage of the reaction.Their decomposition by the SN1 mechanism with ligand transfer in the coordination sphere is a highly selective process and leads to one or the other oxidation products.
