24237-68-1Relevant academic research and scientific papers
Orbital distortion arising from remote substituents. Nitration, reduction, and epoxidation of fluorenes bearing a carbonyl or an olefin group in spiro geometry
Ohwada, Tomohiko
, p. 8818 - 8827 (1992)
Nitration of spiro[cyclopentane-1,9′-fluoren]-2-one with acetyl nitrate predominantly gave the 4-nitro derivative. In the reduction of substituted spiro[cyclopntane-1,9′-fluoren]-2-ones, the anti alcohols were favored in all cases. In the epoxidation of substituted spiro[cyclopent-2-ene-1,9′-fluorenes], the syn epoxides were favored. These distributions of the products can be interpreted in terms of orbital perturbations arising from interactions of the π orbitals of the aromatic and the carbonyl moieties or of the π orbitals of the aromatic and the olefin moieties, i.e., orbital mixing perturbation of the aromatic π orbitals through the π orbital of the bisected carbonyl (or olefin) group and the reciprocal perturbation of the π orbital of the carbonyl (or olefin) group arising from the orthogonal π aromatic orbitals.
Nitration of polycyclic aromatic hydrocarbons using a supported catalyst
Smith, Amy C.,Narvaez, Lorena D.,Akins, Bridget G.,Langford, Moses M.,Gary, Thomas,Geisler, Victoria J.,Khan, Farooq A.
, p. 4187 - 4192 (2007/10/03)
We report the use of a catalyst, sulfuric acid supported on silica-gel, as a promising method for facile, high yielding, regioselective syntheses of mononitrated polycyclic aromatic hydrocarbons, 6-nitrochrysene, 1- nitropyrene, 1-nitronaphthalene, 2-nitrofluorene, 3-nitrofluoranthene, and 9- nitroanthracene.
