Meisenheimer rearrangement

In organic chemistry, the Meisenheimer rearrangement is the conversion of a tertiary amine oxide to a alkoxylamine. The reaction is most common for benzylic or allylic amine oxides.[1][2] The reaction is names for Jakob Meisenheimer.[3] The process resembles the oxy-Cope rearrangement.

The 1,2-rearrangement:

The 2,3-rearrangement:

References

  1. ^ Smith, Michael B.; March, Jerry (2001). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (5th ed.). Wiley-Interscience. p. 1623. ISBN 0-471-58589-0.
  2. ^ Buston, Jonathan E. H.; Coldham, Iain; Mulholland, Keith R. (1999). "Meisenheimer rearrangements of N-allyl 2-azabornane derivatives". Journal of the Chemical Society, Perkin Transactions 1 (16): 2327–2334. doi:10.1039/A903050F.
  3. ^ Meisenheimer, Jakob (1919). "Über eine eigenartige Umlagerung des Methyl-allyl-anilin- N -oxyds". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 52 (8): 1667–1677. doi:10.1002/cber.19190520830.
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