13041-62-8Relevant articles and documents
Behavior of naphthoyloxyl and methoxynaphthoyloxyl radicals generated from the photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones
Najiwara, Toshihiro,Hashimoto, Ji-ichiro,Segawa, Katsunori,Sakuragi, Hirochika
, p. 575 - 585 (2007/10/03)
1-Naphthoyloxyl and 2-naphthoyloxyl radicals were generated from photocleavage of dinaphthoyl peroxides and 1-(naphthoyloxy)-2-pyridones in acetonitrile. The difference in product distribution between the precursors is ascribed to the contribution of the two-bond cleavage in the peroxide decomposition in the singlet state. A series of methoxynaphthoyloxyl radicals were also generated from the corresponding (methoxynaphthoyloxy)pyridones and their behavior was compared with that of unsubstituted naphthoyloxyl radicals. The introduction of a methoxy group in the naphthalene ring stabilizes the naphthoyloxyl radicals to prevent their decarboxylation completely and reduces remarkably their reactivities in the addition to olefins and hydrogen-atom abstraction. The structure of the naphthoyloxyl radicals was discussed on the basis of their absorption spectra and MO calculations.
Photochemical Nitration by Tetranitromethane. Part XXII. Adducts as Precursors of Nitro Substitution Products from the Photolysis of 1-Methoxynaphthalene-Tetranitromethane, Dehydrodimer Formation and the Regiochemistry of Trinitromethanide Ion Attack on the Radical Cation of ...
Butts, Craig P.,Eberson, Lennart,Hartshorn, Michael P.,Persson, Ola,Robinson, Ward T.
, p. 253 - 264 (2007/10/02)
The photolysis of 1-methoxynaphthalene with tetranitromethane in dichloromethane at 20 deg C gives mainly 1-methoxy-4-nitronaphthalene (2) and 1-methoxy-4-trinitromethylnaphthalene (5), together with smaller amounts of 1-methoxy-2-nitronaphthalene (1) and the two adducts, 4-methoxy-r-1-nitro-t-2-trinitromethyl-1,2-dihydronaphthalene (6) and 4-methoxy-r-2-nitro-t-1-trinitromethyl-1,2-dihydronaphthalene (7).Photolysis in the presence of trifluoroacetic acid under otherwise identical conditions gives initially exclusively 4,4'-dimethoxy-1,1'-binaphthalene (10) as the product, trinitromethanide ion being eliminated as a reactant by protonation to give nitroform.EPR spectral and cyclic voltammetric data indicate that the radical cation 10 is present in this reaction.Evidence is presented that, in the absence of trifluoroacetic acid, the reaction products 1, 2 and 5 all arise by decomposition of highly labile nitro-trinitromethyl or nitrito-trinitromethyl adducts 11, 12 and 14.The regiochemistry of attack of trinitromethanide ion on the radical cation of 1-methoxynaphthalene is discussed, and it is proposed that this step is reversible, the regiochemistry of attack being determined by the relative energies of the carbon radicals formed in the process.X-Ray crystal structures are reported for 1-methoxy-4-trinitromethylnaphthalene (5) and 4,4'-dimethoxy-1,1'-binaphthalene (10).
Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid
Nishino, Hiroshi,Tsunoda, Katsunori,Kurosawa, Kazu
, p. 545 - 550 (2007/10/02)
The reaction of naphthlenes with malonic acid in the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids.Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products.It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl radical formed by the interaction of malonic acid and manganese(III) acetate.In addition, it was also found that the dicarboxymethyl radicals attacked the position of the highest electron density on the aromatic ring and that this formylation was effective when the ionization potential of the aromatic copound was lower than 7.8 eV.
