Stepwise construction of a 4-hydroxyphenyl functionalized O,N,N-tridentate ferrocene-containing enaminone: Spectral, analytical and structural studies

Salvador Celedon, MAURICIO DANIEL FUENTEALBA CARRASCO, Thierry Roisnel, Jean René Hamon, David Carrillo, Carolina Manzur

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26 Scopus citations

Abstract

Tetrahydropyranylation of methyl-4-hydroxybenzoate proceeds with formation of its corresponding THP aromatic ether THP-O-p-C 6H 4CO 2CH 3 (1; THP = tetrahydropyranyl, C 5H 9O). Reaction with in situ generated carbanion of acetylferrocene gave the protected organometallic complex Fc-C(O)CHC(OH)(p- C 6H 4-O-THP) (2, Fc(η 5-C 5H 5)Fe(η 5-C 5H 4)) featuring keto-enol functionality; subsequent acidic treatment of 2 afforded the 4-hydroxyphenyl substituted counterpart Fc-C(O)CHC(OH)(p-C 6H 4OH) (3) that exists as a 73/27 mixture of keto-enol/β-diketone tautomers in DMSO solution. The functionalized tridentate metalloligand Fc-C(O)CHC(p-C 6H 4OH)N(H)CH 2CH 2NH 2 (4) incorporating O,N,N-donors is readily obtained upon Schiff base condensation of 3 with 1,2-diaminoethane. Complex 4 exists exclusively as its ferrocenyl-enaminone tautomer in solution and in the solid state. Compounds 1-4 were characterized by NMR ( 1H, 13C) and IR spectroscopy as well as by elemental analysis and single-crystal X-ray diffraction.

Original languageEnglish
Pages (from-to)184-189
Number of pages6
JournalInorganica Chimica Acta
Volume390
DOIs
StatePublished - 15 Jul 2012

Keywords

  • Enaminone
  • Ferrocene
  • Metalloligand
  • O,N,N ligand
  • Tridentate ligand
  • X-ray structure

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