The Wagner – Meerwein rearrangement is the general name for reactions with a 1,2-migration of a functional group to a carbocation center that occurs in a molecule during nucleophilic substitution , addition to a multiple bond, or elimination reactions.
Hydrocarbons and their derivatives, which have a branched carbon skeleton, enter this reaction. In alicyclic compounds, rearrangement is often accompanied by a change in cycle size.
With an increase in the dielectric constant of the solvent and a decrease in the basicity of the solvent, the rearrangement reaction accelerates. Strong binding of the leaving anion, for example, in the form of the complex ion [AlCl 4 ] - or [SbCl 6 ] - , also increases the likelihood of a reaction.
The reaction was discovered by E. E. Wagner in 1899 and was investigated in detail by H. Meerwein in 1910-1927 [1] .
Content
- 1 Reaction Examples
- 2 Application
- 3 Literature
- 4 notes
Reaction Examples
- Camphenic rearrangements of the first kind.
- Isomerization with simultaneous dehydration of alcohols .
Application
- Getting camphor from α- pinene :
- Obtaining isobornyl acetate from camphene .
- Synthesis of Santalidol .
Literature
- Wagner, GJ Russ. Phys. Chem. Soc. 1899, 31, 690.
Notes
- ↑ Knunyants I.L. (Ch. Ed.). Chemical Encyclopedia: in 5 vols. - M .: Soviet Encyclopedia. - T. 1. ABL-DAR. - S. 659-660.