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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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.[1][2] Several reviews have been published.[3][4][5] … Wikipedia
wagner-meerwein rearrangement — noun see wagner rearrangement … Useful english dictionary
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Wagner — Cette page d’homonymie répertorie les différents sujets et articles partageant un même nom. Patronyme Pour consulter un article plus général, voir : Nom de famille germanique. Wagner est un nom de famille (signifiant charron) porté par … Wikipédia en Français
1,2-rearrangement — A 1,2 rearrangement or 1,2 migration or 1,2 shift or Whitmore 1,2 shift cite journal | title = The common basis of molecular rearrangements | first = Frank C. | last = Whitmore | journal = J. Am. Chem. Soc. | date = 1932 | volume = 54 | issue = 8 … Wikipedia
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