Functionalised acyl ferrocenes: Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene

A. Bényei, Christopher Glidewell, Philip Lightfoot, Brodyck J L Royles, David M. Smith

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.

Original languageEnglish
Pages (from-to)177-186
Number of pages10
JournalJournal of Organometallic Chemistry
Volume539
Issue number1-2
Publication statusPublished - Jul 1 1997

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ferrocenes
Molecular Structure
Molecular structure
Hydrogen
Hydrogen bonds
molecular structure
Crystal structure
hydrogen bonds
acylation
Acylation
crystal structure
Molecules
Chlorides
molecules
chlorides
synthesis
ferrocene
aluminum chloride
1,1,2-trichloroethane

Keywords

  • 1,1′-bis(4-hydroxybenzoyl)ferrocene
  • 4-aminobenzoylferrocene
  • 4-hydroxybenzoylferrocene
  • Acyl ferrocenes
  • Crystal structure
  • Molecular structure

ASJC Scopus subject areas

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

Cite this

Functionalised acyl ferrocenes : Crystal and molecular structures of 4-aminobenzoylferrocene, 4-hydroxybenzoylferrocene and 1,1′-bis(4-hydroxybenzoyl)ferrocene. / Bényei, A.; Glidewell, Christopher; Lightfoot, Philip; Royles, Brodyck J L; Smith, David M.

In: Journal of Organometallic Chemistry, Vol. 539, No. 1-2, 01.07.1997, p. 177-186.

Research output: Contribution to journalArticle

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abstract = "Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.",
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N2 - Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.

AB - Improved methods of synthesis are reported for FcCOC6H4F-4 1a, FcCOC6H4OMe-4 1b and Fcd(COC6H4OMe-4)2 2b [Fc = (C5H5)Fe(C5H4); Fcd = (C5H4)Fe(C5H4)]: demethylation of 1b and 2b, using AlCl3 in 1,1,2-trichloroethane, yields FcCOC6H4OH 1f and Fcd(COC6H4OH)2 2f respectively. Acylation of ferrocene using 4-phthalimidobenzoyl chloride yields 4-(phthalimidobenzoyl)ferrocene 1c, hydrazinolysis of which yields FcCOC6H4NH2-4 1d. Crystal structures are reported for 1d, 1f and 2f: in 1d and 1f the molecules are linked into spiral chains by means of N-H ⋯ O=C and O-H ⋯ O=C hydrogen bonds respectively; in 2f the O-H ⋯ O=C hydrogen bonds link the centrosymmetric molecules into continuous two-dimensional nets, two independent sets of which are interwoven.

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