Wagner-Meerwein rearrangement


Wagner-Meerwein rearrangement

A Wagner-Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon. [Wagner, G. "J. Russ. Phys. Chem. Soc." 1899, "31", 690.] [cite journal
author = Hans Meerwein
title = Über den Reaktionsmechanismus der Umwandlung von Borneol in Camphen; [Dritte Mitteilung über Pinakolinumlagerungen.]
journal = Justus Liebig's Annalen der Chemie
year =1914
volume =405
pages =129–175
doi = 10.1002/jlac.19144050202
]

Several reviews have been published. [Popp, F. D.; McEwen, W. E. "Chem. Rev." 1958, "58", 375. (Review)] [Cargill, R. L. "et al." "Accts. Chem. Res." 1974, "7", 106-113. (Review)] [Olah, G. A. "Accts. Chem. Res." 1976, "9", 41. (Review)] [Hogeveen, H.; Van Krutchten, E. M. G. A. "Top. Curr. Chem." 1979, "80", 89-124. (Review)] [Hanson, J. R. "Comp. Org. Syn." 1991, "3", 705-719. (Review)]

The rearrangement was first discovered in bicyclic terpenes for example the conversion of isoborneol to camphene [JerryMarch] :

The related Nametkin rearrangement named after Sergey Namyotkin involves the rearrangement of methyl groups in certain terpenes. In some cases the reaction type is also called a retropinacol rearrangement (see Pinacol rearrangement).

References

ee also

* Demjanov rearrangement
* Pinacol rearrangement


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