Arene Iron Complexes in Organic Synthesis. New Routes to Benzophenones, Diaryl Selenides, Xanthones and Thioxanthones

J Peter Storm

Research output: ThesisDoctoral Thesis (compilation)


A multi-step route to unsymmetrically substituted benzophenones based on cationic hapto6-arene-hapto5-cyclopentadienyl iron complexes has been developed. The key features are nucleophilic aromatic substitution reactions performed on hapto6-2-chlorocarbomethoxybenzene-hapto5-cyclopentadienyl iron hexafluorophosphate with phenoxides, followed by intramolecular Friedel-Crafts ring-closure. The thus formed xanthone complexes are regioselectively opened, on the iron-coordinated aromatic ring, delivering benzophenone complexes. Regioselective cyanide addition/oxidative demetalation releases heavily substituted benzophenones. A formal total synthesis of the benzophenone appendage of the protein kinase C inhibitor balanol is presented. Xanthones and thioxanthones have been synthesised via nucleophilic aromatic substitution reactions, with phenoxides or thiophenoxides as nucleophiles, performed on hapto6-2-chloro-N,N-diethylbenzamide-hapto5-cyclopentadienyl iron hexafluorophosphate. Photolytic decomplexation followed by Directed remote Metalation delivers the heterocycles. A new synthetic method for the preparation of diaryl selenides based on nucleophilic aromatic substitution reactions performed on hapto6-chloroarene transition metal complexes has been developed. The preparation of hapto6-trifluoromethanesulphonylbenzene-hapto5-cyclopentadienyl iron hexafluorophosphate and its reactivity in SNAr reactions or palladium-catalysed trans-formations is described.
Original languageEnglish
Awarding Institution
  • Centre for Analysis and Synthesis
  • [unknown], [unknown], Supervisor, External person
Award date2000 Nov 24
ISBN (Print)91-7874-081-9
Publication statusPublished - 2000

Bibliographical note

Defence details

Date: 2000-11-24
Time: 10:15
Place: Centre for Chemistry and Chemical Engineering

External reviewer(s)

Name: Stephenson, G. Richard
Title: Dr
Affiliation: University of East Anglia, Norwich, U.K.


Article: I Nilsson, J. P.; Andersson, C.-M.A Divergent Route to Substituted Benzophenones Based on Cationic h6-(Arene)iron IntermediatesTetrahedron Lett. 1997, 38, 4635-4638.

Article: II Storm, J. P.; Andersson, C.-M.An Organoiron Approach to the Benzophenone Appendage of the Protein Kinase C Inhibitor BalanolOrg. Lett. 1999, 1, 1451-1453.

Article: III Storm, J. P.; Andersson, C.-M.Iron-Mediated Synthetic Routes to Unsymmetrically Substituted, Sterically Congested BenzophenonesJ. Org. Chem. 2000, 65, 5264-5274.

Article: IV Vasil'ev, A. A.; Engman, L.; Storm, J. P.; Andersson, C.-M.Preparation of Unsymmetrical Diaryl Selenides via SNAr Reactions in h6-Chloroarene Transition Metal ComplexesOrganometallics 1999, 18, 1318-1325.

Article: V Storm, J. P.; Ionescu, R. D.; Martinsson, D.; Andersson, C.-M.A New Route to Xanthones and Thioxanthones Based on h6-2-Chloro-N,N-Diethylbenzamide-h5-Cyclopentadienyl Iron HexafluorophosphateSynlett 2000, 975-978.

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)

Subject classification (UKÄ)

  • Organic Chemistry


  • Directed remote Metalation
  • nucleophilic aromatic addition
  • nucleophilic aromatic substitution
  • Arene-iron complexes
  • balanol
  • Organic chemistry
  • Organisk kemi


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