37496-00-7Relevant academic research and scientific papers
Direct Oxidation of Arenes to Arene Oxides by 2-Nitrobenzene Peroxysulfur Intermediate Generated from 2-Nitrobenzenesulfonyl Chloride and Superoxide
LEE, Hyeon Kye,KIM, Kyoung Soo,KIM, Jack C.,KIM, Yong Hae
, p. 561 - 564 (1988)
Acenaphthylene, phenanthrene, and pyrene, which are inert with superoxide itself, were readily oxidized to the corresponding arene oxides by a 2-nitrobenzene sulfonyl-peroxyl radical intermediate (A) generated from 2-nitrobenzenesulfonyl chloride and potassium superoxide in polar aprotic solvents such as acetonitrile, nitromethane, and dimethylformamide under mild conditions.
Epoxidation of polyaromatics using HOF·CH3CN
Rozen, Shlomo,Bareket, Yifat,Blum, Jochanan
, p. 2333 - 2334 (1997)
The reaction of the HOF·CH3CN complex, made directly by passing fluorine through aqueous acetonitrile, with some phenanthrene and pyrene derivatives results in fast epoxidation.
Oxidations by methyl(trifluoromethyl)dioxirane. 4.1 Oxyfunctionalization of aromatic hydrocarbons
Mello, Rossella,Ciminale, Francesco,Fiorentino, Michele,Fusco, Caterina,Prencipe, Teresa,Curci, Ruggero
, p. 6097 - 6100 (1990)
By using the title dioxirane (1a), naphthalene (2), phenanthrene (3), and anthracene (4) have been converted into anti-naphthalene-1,2;3,4-dioxide (2′), phenonthrene-9,10-oxide (3′), and anthraquinone (4′), respectively, in high yield and under mild conditions. However, the transformation of pyrene (5) - an higher homologue of the polycyclic aromatic hydrocarbon series - into the corresponding arene oxide was found to proceed much less effectively.
GENERAL SYNTHETIC ROUTES TO DIARENE OXIDES OF POLYCYCLIC AROMATIC HYDROCARBONS
Agarwal, Shiv K.,Boyd, Derek R.,Jennings, W. Brian,McGuckin, Rosaleen M.,O'Kane, Gerard A.
, p. 123 - 126 (2007/10/02)
Diarene oxides have been synthetized by a single step oxidation of monoarene oxides using dimethyldioxirane, and by a three step cyclization sequence from the appropriate trans-tetrahydrobromoacetate precursors.
DIRECT EPOXIDATION OF POLYCYCLIC AROMATIC COMPOUNDS BY SUPEROXIDE IN THE PRESENCE OF PHOSGENE DIMER
Nagano, Tetsuo,Yokoohji, Kiyomi,Hirobe, Masaaki
, p. 3481 - 3484 (2007/10/02)
Olefins and polycyclic aromatic compounds were oxidized to their epoxides by superoxide (O2-.) in the presence of phosgene dimer.The reaction mechanisms are discussed.
Model Systems for Cytochrome P450 Dependent Mono-oxygenases. Part 1. Oxidation of Alkenes and Aromatic Compounds by Tetraphenylporphinatoiron(III) Chloride and Iodosylbenzene
Smith, John R. Lindsay,Sleath, Paul R.
, p. 1009 - 1016 (2007/10/02)
A selection of aliphatic alkenes, substituted styrenes, and cis- and trans-stilbene have been epoxidised with tetraphenylporphinatoiron(III) chloride and iodosylbenzene, a model system for the cytochrome P450 dependent mono-oxygenases.The epoxidations are stereospecifically syn and the reactivities of the alkenes show that cis-alkenes are more reactive than their trans-isomers and that electron-releasing substituents favour the reaction.A Hammett ρ value of -0.93 is obtained from the epoxidation of the substituted styrenes.Three polycyclic hydrocarbons, phenanthrene, acenaphthylene, and pyrene, are epoxidised in low yield.The model system hydroxylates anisole and naphthalene but is insufficiently reactive to oxidise benzene; with toluene, side-chain oxidation but no ring hydroxylation occurs.The mechanisms of these oxidations and the nature of the reactive species are discussed.
