78787-97-0Relevant academic research and scientific papers
Multielectron oxidation of anthracenes with one-electron oxidant via water-accelerated electron-transfer disproportionation of the radical cations as the rate-determining step
Fukuzumi,Nakanishi,Tanaka
, p. 11212 - 11220 (1999)
The six-electron oxidation of anthracene and the four-electron oxidation of 9-alkylanthracene occurred with [Ru(bpy)3]3+ (bpy = 2,2-bipyridine) in acetonitrile (MeCN) containing H2O to yield anthraquinone and 10-alkyl-10-h
Electron-Transfer Oxidation of 9-Alkylanthracenes and the Decay Kinetics of Radical Cations in Acetonitrile
Fujita, Morifumi,Fukuzumi, Shunichi
, p. 1911 - 1914 (1993)
Transient absorption spectra of radical cations of 9-alkylanthracenes (RAn+) formed by the electron-transfer oxidation of 9-alkylanthracenes with Fe(ClO4)3*9H2O have been detected by using a stopped flow spectrophotometer.The decay rates of RAn
Competition between nucleophilic addition and electron-transfer process in the reaction of 9-diazo-10-anthrone with Grignard reagents
Bruni, Paolo,Carloni, Patricia,Conti, Carla,Giorgini, Elisabetta,Greci, Lucedio,Iacussi, Marco,Stipa, Pierluigi,Tosi, Giorgio
, p. 6795 - 6802 (2007/10/03)
9-diazo-10-anthrone reacts with RMgX (R = Me, Et, Bu(n), 5-hexenyl, Pr(i), benzyl, Bu(t)) essentially yielding 9-alkylazo-10-hydroxy derivatives, which are isolated in their tautomeric quinoid structure as alkylhydrazones of 9,10-anthraquinone. The yields of these compounds decrease as the oxidation potentials (E(OX) of the Grignards decrease: at the same time additional compounds, formed through a radical mechanism, are obtained in higher yields. The reaction has been interpreted as a competition between single electron transfer (SET) and nucleophilic attack, which occur with ratios varying with the oxidation potentials of the Grignard reagents. Evidences for the SET pathway have been found performing an experiment in the presence of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a scavenger of C-centered radicals.
Regioselective Alkylation of Anthrahydroquinone and Anthrone in Water with Quinonemethides and Other Alkylating Agents
Dimmel, Donald R.,Shepard, Donaline
, p. 22 - 29 (2007/10/02)
Antrahydroquinone (AHQ) and anthrone are alkylated in the C10 position by quinonemethides, generated in situ from p-acetoxybenzyl chlorides, to give adducts 13-15, 24, 25, 28, 29, and 32.Aqueous alkylations of AHQ with methyl vinyl ketone, cinnamaldehyde, and benzyl chloride also produces C10-substituted 10-hydroxyanthrones.Simple ketones and aldehydes do not, however, alkylate AHQ in aqueous alkali.
