Abstract
Diels−Alder addition of diphenylacetylene or of 1,2,3-triphenylcyclopropene to 3-ferrocenyl-2,4,5-triphenylcyclopentadienone yields, upon thermolysis, C6Ph5Fc (5) or C7Ph6FcH (8), respectively. Subsequent treatment of 8 with triethyloxonium hexachloroantimonate results in the formation of the ferricinium complex [C7Ph6FcH]+[SbCl6]- (13), rather than the anticipated tropylium cation [C7Ph6Fc]+. The substituted ferrocene derivatives 5, 8, and 13 have been characterized by X-ray crystallography. From the solid-state structure of 5 it is evident that the peripheral aryl substituents do not adopt a regular propeller type conformation, but instead exhibit an incremental progression of twist angles relative to the central ring. The dynamics of peripheral ring rotations in 5 and 8 have been studied by variable-temperature NMR.
Published Version
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