10519-73-0Relevant articles and documents
Deprotonation of Methylarene Cation Radicals in Acetonitrile. An Unexpected Second-Order Mechanism
Parker, Vernon D.,Tilset, Mats
, p. 6371 - 6377 (1986)
The kinetics of the deprotonation reactions of the cation radicals of several methylarenes were studied by derivative cyclic voltammetry (DCV) and derivative linear-sweep voltammetry (DLSV) in acetonitrile.The kinetic data indicate rate law and suggest a
KINETICS AND MECHANISM OF AROMATIC OXIDATIVE SUBSTITUTIONS VIA ELECTRON TRANSFER. APPLICATION OF MARCUS THEORY TO ORGANIC PROCESSES IN THE ENDERGONIC REGION
Schlesener, C.J.,Amatore, C.,Kochi, J.K.
, p. 3567 - 3577 (1984)
Oxidative substitution of methylarenes by iron(III) complexes proceeds via initial electron transfer to afford benzylic products in excellent yields.The growth and decay of the cation radical ArCH3(1+) (as the prime transient intermediate) are observed
Remarkable effect of water on functionalization of the phenyl ring in methyl-substituted benzene derivatives with F-TEDA-BF4
Kralj, Petra,Zupan, Marko,Stavber, Stojan
, p. 3880 - 3888 (2007/10/03)
Various N-F reagents reacted with hexamethylbenzene (1) forming side chain substituted alkoxides or esters in protic solvents, Ritter type side chain functionalization was observed in acetonitrile in the presence of trifluoroacetic acid, while in aqueous
Structural Effects in the TiO2-Photocatalyzed Oxidation of Alkylaromatic Compounds in Acetonitrile in the Presence of Ag2SO4
Baciocchi, Enrico,Rol, Cesare,Sebastiani, Giovanni V.,Taglieri, Luca
, p. 5272 - 5276 (2007/10/02)
The TiO2-sensitized photochemical reactions of some alkylbenzenes (ArCH2R; R = H, Me), 1-aryl-2-propanols, and corresponding methyl esters (ArCH2C(OR'')R'CH3; R', R'' = H, Me) have been investigated in MeCN, in the presence of Ag2SO4, which traps the photogenerated electrons.With ArCH2R, the corresponding radical cations are generated by the photoexcited TiO2 and are then deprotonated to from benzyl radicals; from the latter 1,2-diarylethanes, 3-arylpropanonitriles, and benzylacetamides are obtained as major products.With ArCH2C(OR'')R'CH3, the formed radical cations undergo C-C bond cleavage as the only observed route, when Ar = Ph.However, when Ar = 4-MeOPh and R' = H, the radical cation undergoes C-H bond cleavage as the major or exclusive reaction path.These results are compared with those obtained in the corresponding homogeneous photochemical reactions, and their implications with respect to the role of the structure on the side-chain reactivity of aromatic radical cations are discussed.