24237-68-1Relevant articles and documents
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 Polyciclic Aromatic Hydrocarbons with Dinitrogen Tetroxide. A Simple and Selective Synthesis of Mononitro Derivatives
Radner, Finn
, p. 65 - 68 (2007/10/02)
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