Synthesis of substituted 1,1′-diaminoferrocenes from cyclo-2-pentene imines

Katharina R. Nikolaides, Stephan D. Hoffmann, Jorg Eppinger*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Condensation of anilines and primary aliphatic amines with 3,4-diphenylcyclo-2-pentenone leads to the corresponding diphenylcyclopentene imines in good yields of 72-90%. Deprotonation of these aminocyclopentadiene tautomers and reaction with FeCl2 leads to the synthesis of the respective 1,1′-diamino-3,3′,4,4′-tetraphenylferrocenes. Yields increase from 33% to 65% with a decrease in the steric bulk of the amine substituent. The observation that a successful conversion requires two equivalents of base is conceived on the basis of the discussed reaction mechanism. The molecular structure of 1,1′-dianilino-3,3′,4,4′-tetraphenylferrocene (3a), which was determined by single crystal X-ray analysis reveals a trans coordination of the two amine moieties with respect to the central Cp-Fe-Cp axis of the ferrocenyl backbone.

Original languageEnglish (US)
Pages (from-to)2223-2230
Number of pages8
JournalJournal of Organometallic Chemistry
Volume693
Issue number13
DOIs
StatePublished - Jun 15 2008

Keywords

  • Aminoferrocene
  • Diamines
  • Ferrocene
  • Silylamide route

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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