Synthesis of ferrocenyl quinones

A squarate-based synthesis of ferrocenyl quinones is described. Thermolysis of ferrocenyl-substituted cyclobutenones, prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl cyclobutenediones have been prep...

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Bibliographic Details
Published in:Tetrahedron letters 2003-03, Vol.44 (10), p.2237-2241
Main Authors: Zora, Metin, Yucel, Baris, Acikalin, Serdar
Format: Article
Language:English
Subjects:
cyclobutenediones
cyclobutenols
cyclobutenones
electrocyclization
ferrocenes
ferrocenyl quinones
hydroquinones
oxidation
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Summary:A squarate-based synthesis of ferrocenyl quinones is described. Thermolysis of ferrocenyl-substituted cyclobutenones, prepared from ferrocenyl cyclobutenediones and alkenyllithiums, affords hydroquinones, which furnish, upon oxidation, ferrocenyl quinones. Ferrocenyl cyclobutenediones have been prepared from known cyclobutenediones by nucleophilic addition of ferrocenyllithium followed by hydrolysis, Pd/Cu-cocatalyzed cross-coupling with (tri- n-butylstannyl)ferrocene or Friedel–Crafts alkylation with ferrocene. A squarate-based synthesis of ferrocenyl quinones is described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)00099-6