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MOESSBAUER STUDIES ON FERROCENE COMPLEXES. XIV. CARBENIUM IONS AND KETONES OF <3>FERROCENOPHANES
A series of <3>ferrocenophane(FcP) derivatives have been investigated using 57Fe Moessbauer and 1H NMR spectroscopy.For the 2- and 3-acetyl-FcP in neutral and acidic mrdia, proton resonances were assigned by analogy with the unbridged species, which themselves were analysed using specifically alpha deuteriated compounds. 2-Acetyl-FcP exhibited a strongly shielded methyl group due to out of plane deformation of the carbonyl function.The corresponding carbenium ions were produced from the parent alcohols in CF3CO2 and their NMR spectra discussed. <3>Ferrocenophan-6,8-dione(A) was unprotonated in CF3CO2H, monoprotonated in 80percent H2SO4 to give the symmetrical carbenium ion.The NMR spectrum of the ion is fully discussed.Moessbauer spectra of 2- and 3-acetyl-FcP revealed the latter to have an anomalously low value of both quadrupole splitting (QS) and isomer shift (IS).The QS of frozen solutions of A at pH 13 show little change from those of ferrocene indicating that the carbanionic charge creates a symmetrical electron density about the iron atom by repulsion of the r2g electrons.The carbenium ion generated at the 2 position in <3>FcP showed a higher QS than that in the 3-position due to better overlap with e2g orbitals.The symmetrical carbenium ion derived from dehydro-<3>ferrocenophane showed exalted QS values indicative of iron e2g orbital overlap.The effect of bridging on Moessbauer parameters is also discussed.
MOESSBAUER STUDIES ON FERROCENE COMPLEXES. XIV. CARBENIUM IONS AND KETONES OF <3>FERROCENOPHANES
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Reference£º
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion