434-84-4Relevant academic research and scientific papers
Electrolysis at an Anthracene Crystal/Aqueous NO3- Solution Interface: The Role of Crystal Defects
Pope, M.,Mao, B.,Steigman, J.,Geacintov, N. E.
, p. 1719 - 1720 (1990)
The electrolysis of a 1 M solution of NaNO3 by means of an anthracene crystal electrode results in the production of many surface reaction products, including 9-nitroanthracene (9NA), bianthronyl (BA), and anthraquinone (AQ).The production of 9NA and BA have been shown to depend on the square of the current density.This dependence was rationalized by hypothesizing the need for the simultaneous discharge of two carriers at adjoining lattice defect sites.By annealing the crystals, it was found that the efficiency of producing 9NA was reduced by a factor of as much as 6; this supports the hypothesis.
Photophysics and Photochemistry of Nitroanthracenes. Part 2. Primary Process in the Photochemical Reaction of 9-Nitroanthracene studied by Steady-state Photolysis and Laser Photolysis
Hamanoue, Kumao,Nakayama, Toshihiro,Kajiwara, Kanji,Yamanaka, Shigenobu,Ushida, Kiminori
, p. 3145 - 3152 (1992)
From measurements of phosphorescence and triplet-triplet absorption spectra of the lowest excited triplet ??* state of 9-nitroanthracene (NA) together with the absorption spectrum of 9-anthryloxy radical, it is concluded that photolysis of 9-nitroanthracene gives rise to the nitro -> nitrite rearrangement for a higher excited triplet state of n?* character, followed by the cleavage of 9-anthryl nitrite to 9-anthryloxy radical and nitrogen(II) oxide, yielding 9-anthrol (and anthrone), 10,10'-bianthrone and 9-nitrosoanthrone in ethanol; and 10,10'-bianthrone and 9-nitrosoanthrone in benzene.Hence, the primary process in the photochemical reaction of NA is essentially identical with those of 9-benzoyl-10-nitroanthracene and 9-cyano-10-nitroanthracene except that no 10,10'-bianthrone derivatives are formed.
Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling
Hosseini, Abolfazl,Schreiner, Peter R.
, p. 4339 - 4346 (2020/07/04)
Ball milling of calcium carbide (CaC2) enables the reaction of its ethynyl moiety with organic electrophiles. This was realized simply by co-milling CaC2 with organic substrates in a sealed jar without the need for an additive or a catalyst. Various ketones including those bearing α-hydrogens were ethynylated in good yields at short reaction times. Aryl halides are also amenable substrates for this protocol as they furnish aryl ethynes through a benzyne intermediate. This method offers a practical and cheap alternative to the established procedures for introducing ethynyl functionalities.
Oxidation of benzyl alcohols, benzyl halides, and alkylbenzenes with oxone
Parida, Keshaba Nanda,Jhulki, Samik,Mandal, Susovan,Moorthy, Jarugu Narasimha
, p. 9763 - 9768,6 (2020/08/20)
Oxidation of benzyl alcohols, benzyl halides, and alkylbenzenes to their corresponding oxidation products has been shown to be accomplished directly with oxone. The methodology that involves mere stirring/heating of the reactants and oxone in acetonitrile/water (1:1, v/v) is simple and practical, but is limited to substrates that do not contain sensitive functionalities and heteroaromatic rings.
Oxidative-substitution reactions of polycyclic aromatic hydrocarbons with iodine(III) sulfonate reagents
Koser, Gerald F.,Telu, Sanjay,Laali, Kenneth K.
, p. 7011 - 7015 (2007/10/03)
Polycyclic aromatic hydrocarbons (PAH) undergo regioselective oxidative-substitution reactions with iodine(III) sulfonate reagents in dichloromethane to give the corresponding aryl sulfonate esters. The use of [hydroxy(tosyloxy)iodo]benzene in conjunction
Efficient pyridinylmethyl functionalization: Synthesis of 10,10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an acetylcholine release enhancing agent
Pesti,Huhn,Yin,Xing,Fortunak,Earl
, p. 7718 - 7722 (2007/10/03)
2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methane-sulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.
Sc(OTf)3- and TfOH-catalyzed baeyer-villiger oxidation of carbonyl compounds with m-chloroperbenzoic acid
Kotsuki, Hiyoshizo,Arimura, Koji,Araki, Tomohiro,Shinohara, Toshio
, p. 462 - 464 (2007/10/03)
An efficient method for Baeyer-Villiger oxidation of carbonyl compounds to the. corresponding esters/lactones has been developed using m-chloroperbenzoic acid in the presence of a catalytic amount of Sc(OTf)3 or TfOH. Thieme Stuttgart.
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.
THE SELECTIVE FUNCTIONALIZATION OF SATURATED HYDROCARBONS. PART 28. THE ACTIVATION OF BENZYLIC METHYLENE GROUPS UNDER GOAGGIV AND GOAGGV CONDITIONS
Barton, Derek H. R.,Wang, Tie-Lin
, p. 1011 - 1032 (2007/10/02)
Under GoAggIV and GoAggV conditions, cyclohexadienes were oxidized to give aromatic products instead of ketones and alcohols.At the same time, anthracene was oxidized to give anthraquinone.Under GoAggIV and GoAggV conditions, xanthene, fluorene and diphenylmethane were oxidized to give the corresponding xanthone, fluorenone and benzophenone following two possible pathways: a) alkane to alkyl t-butylperoxide to ketone, and b) alkane to ketone, in which alkyl hydroperoxide, derived from oxygen, may be the reaction intermediate.Xanthyl azide was formed when sodium azide was added to the reaction mixture of xanthene under GoAggIV and GoAggV conditions.The reaction of triphenylmethane under GoAggV conditions gave triphenylmethyl t-butyl peroxide as the major product and hydroperoxide as the minor product.When TEMPO was added, triphenylmethyl hydroperoxide was the only product.
Oxidation of arenes to para-quinones with hydrogen peroxide catalyzed by hexafluoroacetone hydrate
Adam,Ganeshpure
, p. 280 - 282 (2007/10/02)
Various aromatic hydrocarbons were oxidized with aqueous hydrogen peroxide in the presence of hexafluoroacetone hydrate as catalyst to give para-quinones and/or the ring cleavage oxidation products. The regioselective oxidation of 2-methylnaphthalene to 2-methyl-1,4-naphthoquinone (vitamin K3) was studied in detail.
