2584-79-4Relevant articles and documents
Competitive occurrence of homolytic N-O and heterolytic C-O bond cleavage in excited-state 1-(arylmethyloxy)-2-pyridones
Yoshioka, Nariyoshi,Andoh, Chihei,Kubo, Kanji,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 1927 - 1932 (2007/10/03)
The irradiation at 340 nm of the title compounds having 9-anthryl and pyren-1-yl groups in methanol was found to give the heterolytic C-O bond cleavage products: 1-hydroxy-2-pyridone and aryl-substituted dimethyl ether (which predominate for the reaction of the former title compound) in addition to 2-pyridone, aryl-substituted methanol and aryl-substituted formaldehyde derived from the homolysis of the N-O bond (which mainly occurs in the photolysis of the latter title compound). It was also found that substitution of the methyl group for hydrogen at the 6-position of the pyridone skeleton in 1-(9-anthrylmethyloxy)-2-pyridone decreases the relative composition of the arylsubstituted dimethyl ether to some extent. These substituent effects on the product compositions were explained in terms of stereoelectronic effects on a charge transfer-type interaction between the aromatic and pyridone rings in the singlet excited state. Analyses of the ground-state conformation for the title compounds by MM2 calculations and 1H NMR spectroscopy, as well as of their singlet excited-state behaviour, substantiated the existence of a non-emissive intramolecular exciplex intermediate which plays a key role in inducing the C-O bond heterolysis.
TELE-SUBSTITUTIONS EN SERIE ANTHRACENIQUE - II; EXTENSION DE LA SUBSTITUTION PAR L'ION PHENATE A DIVERS BROMO-9 ANTHRACENES MESO-ALKYLES
Rigaudy, J.,Seuleiman, A.M.,Cuong, Nguyen Kim
, p. 3151 - 3156 (2007/10/02)
A competition between normal substitution and tele-substitution is observed with 9-bromoanthracenes bearing in the opposite meso position an ethyl, 1b, or a benzyl group 1d.When treated with potassium phenoxide in HMPT these bromides afford mixtures of 9-alkyl-10-phenoxy-anthracenes 2 and 9-α(phenoxyalkyl) anthracenes 3.On the other hand 9-bromo-10 isopropylanthracene 1c is quite unreactive and 9-bromo-10-methoxymethylanthracene 1e leads essentyally to anthraldehyde 7.