Meisenheimer rearrangement
| Meisenheimer rearrangement | |
|---|---|
| Named after | Jakob Meisenheimer |
| Reaction type | Rearrangement reaction |
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
[edit]- ↑ 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.
- ↑ 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.
- ↑ 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.