Journal of the American Chemical Society p. 8818 - 8827 (1992)
Update date:2022-08-11
Topics:
Ohwada, Tomohiko
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.
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