Direct one step preparation and 13C-NMR spectroscopic characterization of alpha-ferrocenyl carbocations derived from ferrocene and carbonyl compounds in trifluoroacetic acid medium1a

Reaction of aldehydes and ketones with ferrocene, in the presence of trifluoroacetic acid, afforded a series of stable long lived alpha-ferrocenylalkyl carbocations which were characterized by 13C-NMR spectroscopy. When this reaction was attempted using tetraphenylcyclopentadienone, quite unexpected...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 1999-08, Vol.10 (4), p.313-316
Main Authors: Prakash, G.K. Surya, Buchholz, Herwig A., Vaughan, Julian F.S., Wang, Qi, Olah, George. A.
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:Reaction of aldehydes and ketones with ferrocene, in the presence of trifluoroacetic acid, afforded a series of stable long lived alpha-ferrocenylalkyl carbocations which were characterized by 13C-NMR spectroscopy. When this reaction was attempted using tetraphenylcyclopentadienone, quite unexpectedly the corresponding dihydro derivative 3 was isolated, in very good yield. Formation of this compound may require ferrocene acting as a reducing agent.
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50531999000400010