Chemical Sciences: A Manual for CSIR-UGC National Eligibility Test for Lectureship and JRF/Named Reactions/Wagner-Meerwein Rearrangement

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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.[1][2]

Several reviews have been published.[3][4][5][6][7]

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


Isoborneol Camphene Conversion


The story of the rearrangement reveals that many scientists were puzzled with this and related reactions and its close relationship to the discovery of carbocations as intermediates.[8]

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[edit]

  1. Wagner, G. J. Russ. Phys. Chem. Soc. 1899, 31, 690.
  2. Hans Meerwein (1914). "Über den Reaktionsmechanismus der Umwandlung von Borneol in Camphen; [Dritte Mitteilung über Pinakolinumlagerungen.]". Justus Liebig's Annalen der Chemie 405: 129–175. doi:10.1002/jlac.19144050202. 
  3. Popp, F. D.; McEwen, W. E. Chem. Rev. 1958, 58, 375. (Review)
  4. Cargill, R. L. et al. Accts. Chem. Res. 1974, 7, 106-113. (Review)
  5. Olah, G. A. Accts. Chem. Res. 1976, 9, 41. (Review)
  6. Hogeveen, H.; Van Krutchten, E. M. G. A. Top. Curr. Chem. 1979, 80, 89-124. (Review)
  7. Hanson, J. R. Comp. Org. Syn. 1991, 3, 705-719. (Review)
  8. Birladeanu, L. J. Chem. Ed. 2000, 77, 858-863.