76203-58-2Relevant academic research and scientific papers
INSERTION D'ALLENES. VIII. FORMATION DE CETONES α,β-INSATUREES PAR HYDROACYLATION D'ALLENES EN PRESENCE DE TETRACARBONYL FERRATE DE SODIUM
Roustan, J. L.,Guinot, A.,Cadiot, P.
, p. 367 - 378 (1980)
α,β-Unsaturated ketones are generated in moderate yields (50-60percent) from allene or a mono-, di- or tri-substituted allenic hydrocarbon, an alkyl halide and sodium tetracarbonylferrate.The first step is the formation of a complex anion which results from transfer of the alkyl group on a coordinated CO, then of the acyl ligand thus formed on the allenic sp carbon.Protonation with acetic acid yields a hydroxy-η4-trimethylenemethane, easily isomerised into an η4-heterodieneiron tricarbonyl.Finally, the α,β-unsaturated ketone is released upon oxidation with trimethylamine oxide.The most substituted ketone predominates.
