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SbF5-mediated reactions of oxafluorodiazirines

  1. Author:
    Moss, R. A.
    Fede, J. M.
    Yan, S. Q.

  2. Author Address

    Rutgers State Univ, Dept Chem, New Brunswick, NJ 08903 USA. Rutgers State Univ, Dept Chem, New Brunswick, NJ 08903 USA. NCI, Med Chem Lab, Ctr Canc Res, NIH, Frederick, MD 21702 USA. Moss RA Rutgers State Univ, Dept Chem, New Brunswick, NJ 08903 USA.
    1. Year: 2001
  2. Journal: Organic Letters
    1. 3
    2. 15
    3. Pages: 2305-2308
  4. Type of Article: Article
  1. Abstract:

    [GRAPHICS] The reaction of benzyloxyfluorodiazirine (3) with SbF5 in benzene gives PhCH2OCF, which undergoes SbF5-mediated fragmentation to PhCH2+, CO, and SbF6-; the benzyl cation alkylates benzene to yield diphenylmethane. Phenoxyfluorodiazirine (4) reacts with SbF5 in benzene to give PhOCF and (ultimately) triphenylmethane by a pathway that avoids fragmentation.

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