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Efficient synthesis of ferrocifens and other ferrocenyl-substituted ethylenes <i>via</i> a ‘sulfur approach’
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2018
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EngineeringOrganic ChemistryEfficient SynthesisChemistryHeterocycle ChemistryChemical DerivativeFerrocenyl-substituted EthylenesChemical EngineeringOrganometallic CatalysisAlkyl Ferrocenyl ThioketonesMaterials ScienceDerivatives'Two-fold ExtrusionCatalysisSynthesis MethodEnantioselective SynthesisHeterocyclicOther Ferrocenyl-substituted EthylenesDerivative (Chemistry)Synthetic Chemistry
Stable and non-odorous alkyl ferrocenyl thioketones react with bis(4-methoxyphenyl)diazomethane according to the 'two-fold extrusion' reaction principles, and tetrasubstituted ethylenes obtained thereby can be demethylated to give (Fc,2OH)-ferrocifens in good yields. The method offers an alternative approach to this class of medically relevant compounds. A similar protocol with alkyl ferrocenyl thioketones and selected diaryldiazomethanes leads to ferrocenyl-substituted ethylenes including dibenzofulvenes. These products are of potential interest for electrochemical and photophysical studies.
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