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Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides

Journal Article


Abstract


  • The in situ reduction of ferrocenyl cyclopropylimines to the corresponding amines triggers a facile oxidative ring-opening to yield the formal four-electron oxidation products: N-ferrocenylmethyl β-hydroxyamides. This process is believed to proceed via generation of a ferrocinium ion in the presence of air, leading to facile formation of a distonic radical cation that is ultimately trapped by oxygen.

UOW Authors


  •   Gee, Yi Sing (external author)
  •   Goertz, Neils J. M. (external author)
  •   Gardiner, Michael G. (external author)
  •   Hyland, Christopher

Publication Date


  • 2016

Citation


  • Gee, Y., Goertz, N. J. M., Gardiner, M. G. & Hyland, C. J. T. (2016). Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides. Organic and Biomolecular Chemistry, 14 (8), 2498-2503.

Scopus Eid


  • 2-s2.0-84983165318

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3881

Number Of Pages


  • 5

Start Page


  • 2498

End Page


  • 2503

Volume


  • 14

Issue


  • 8

Abstract


  • The in situ reduction of ferrocenyl cyclopropylimines to the corresponding amines triggers a facile oxidative ring-opening to yield the formal four-electron oxidation products: N-ferrocenylmethyl β-hydroxyamides. This process is believed to proceed via generation of a ferrocinium ion in the presence of air, leading to facile formation of a distonic radical cation that is ultimately trapped by oxygen.

UOW Authors


  •   Gee, Yi Sing (external author)
  •   Goertz, Neils J. M. (external author)
  •   Gardiner, Michael G. (external author)
  •   Hyland, Christopher

Publication Date


  • 2016

Citation


  • Gee, Y., Goertz, N. J. M., Gardiner, M. G. & Hyland, C. J. T. (2016). Oxidative ring-opening of ferrocenylcyclopropylamines to N-ferrocenylmethyl β-hydroxyamides. Organic and Biomolecular Chemistry, 14 (8), 2498-2503.

Scopus Eid


  • 2-s2.0-84983165318

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3881

Number Of Pages


  • 5

Start Page


  • 2498

End Page


  • 2503

Volume


  • 14

Issue


  • 8