86853-91-0Relevant academic research and scientific papers
Study of photochemistry without light of substituted benzylidine acenaphthenones
Goel, Vijender
, p. 301 - 304 (2013/06/27)
In order to draw a parallel between light induced reactions as well as photochemistry without light (chemiluminescence), the substituted benzylidineacenaphthenones were subjected to dioxetanedione reactions, which are formed in situ by the reaction of 2,4-dimitrophenyloxalate with hydrogen peroxide to provide chrysene derivatives as well as naphthalene 1,8-dicarboxylic acid anhydride and benzoic acid whose structures were determined by IR and 1H NMR spectra.
Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation
Gonzalez, Juan J.,Garcia, Nuria,Gomez-Lor, Berta,Echavarren, Antonio M.
, p. 1286 - 1291 (2007/10/03)
The palladium-catalyzed intramolecular arylation reaction has been applied to the synthesis of the spiro polycyclic aromatic hydrocarbons and planar polycyclic aromatic hydrocarbons by formation of a six-membered ring. The reaction proceeds more readily with aryl bromides substituted with electron-withdrawing groups by using palladium acetate in N,N-dimethylformamide as the solvent. For the less reactive p-methoxyaryl derivatives the use of LiI as an additive was shown to give the best results. The results obtained in the cyclization of nitro derivatives 21 and 23 suggest that the second step of the cyclization reaction is not an electrophilic substitution reaction.
Synthesis of Ketone and Alcohol Derivatives of Methylene-Bridged Polyarenes, Potentially New Classes of Active Metabolites of Carcinogenic Hydrocarbons
Harvey, Ronald G.,Abu-shqara, Elias,Yang, ChengXi
, p. 6313 - 6317 (2007/10/02)
Methods for the syntheses of bridge ketone and alcohol derivatives of methylene-bridged polyarenes from the parent hydrocarbons are described.The polyarenes investigated include 4H-cyclopentaphenanthrene (1a), fluorene (2a), 7H-benzofluorene (3a), 4H-cyclopentachrysene (4a), 11H-benzaceanthrylene (5a), 10H-indenopyrene (6a), 11H-dibenzoaceanthrylene (7a), 4H-fluorenoanthracene (8a), and 7H-dibenzofluorene (9a).The bridge ketone derivatives are most efficiently synthesized via treatment of the parent hydrocarbons with n-butyllithium and reaction of the resulting anionic intermediate s with molecular oxygen.The direct formation of ketones rather than the expected hydroperoxides from reaction of the bridge anions with O2 presumably involves intra- or intermolecular abstraction of a proton from the benzylic site of the intermediate by the peroxy anion leading to loss of hydroxide ion with formation of a carbonyl group.Yields are generally high except in the cases of 1a and 4a; the former affords as the principal product a dimeric alcohol arising from reaction of the anion of 1a with the corresponding ketone 1b.The related bridge alcohols are readily obtained in yields of 75-95percent by reduction of the crude products from the preceding oxidations with NaBH4.
