Reactive carbon nucleophiles add to tricarbonyl(η4-1,3-diene)iron(O) complexes at -78°C to produce putative internally coordinated tricarbonyl(η1,η2-but-3-en-1-yl)iron(O) anion complexes. Treatment of the reactive intermediates with bromine, followed by an aqueous process, leads to γ,δ-unsaturated acids. Reaction of the intermediates with iodomethane or benzyl bromide gives γ,δ-unsaturated ketones after carbonyl insertions. Benzoyl chloride is also observed to react with the postulate intermediates to form γ,δ-unsaturated benzophenone derivatives.
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