Communication

Fluorophenoxycarbene inside a Hemicarcerand: A Bottled Singlet Carbene†

  1. Xuejun Liu,
  2. Gaosheng Chu Dr.,
  3. Robert A. Moss Prof.,
  4. Ronald R. Sauers Prof.,
  5. Ralf Warmuth Prof.

Article first published online: 21 FEB 2005

DOI: 10.1002/anie.200462633

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 44, Issue 13, pages 1994–1997, March 18, 2005

Additional Information

How to Cite

Liu, X., Chu, G., Moss, R. A., Sauers, R. R. and Warmuth, R. (2005), Fluorophenoxycarbene inside a Hemicarcerand: A Bottled Singlet Carbene. Angew. Chem. Int. Ed., 44: 1994–1997. doi: 10.1002/anie.200462633

Author Information

  1. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, NJ 08854, USA, Fax: (+1) 732-445-5312

  1. †

    This research was supported by the NSF (Grants CHE-0431749 to R.W. and CHE-0345240 to R.A.M.) and Rutgers University. We thank Dr. Seho Kim for assistance with NMR spectroscopic experiments and Prof. Karsten Krogh-Jespersen for helpful suggestions.

Publication History

  1. Issue published online: 16 MAR 2005
  2. Article first published online: 21 FEB 2005
  3. Manuscript Received: 17 NOV 2004

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Keywords:

  • carbenes;
  • host–guest systems;
  • NMR spectroscopy;
  • photolysis;
  • reactive intermediates
Thumbnail image of graphical abstract

Long live the carbene: Longevity is granted to fluorophenoxycarbene when it is generated photochemically from fluorophenoxydiazirine (see picture) inside a hemicarcerand. This fleeting, and otherwise nonisolable, singlet carbene is the first electron-deficient species that has been stabilized by trapping. NOE experiments suggest that the carbene adopts the intrinsically less stable cis conformation in the confined inner phase.

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