Prior to hydride transfer, the carbocation intermediate is liable to undergo Wagner-Meerwein rearrangements.
2.
Finally, a 1, 2-hydride shift via a Wagner-Meerwein rearrangement produces the terpinen-4-yl cation.
3.
The aglycon is prepared by enzymatic hydrolysis, since upon acid treatment steviol will undergo Wagner-Meerwein rearrangement to the very stable isosteviol.
4.
For alkenes, the reaction gives carbonyl products, though the mechanistic process is not simply epoxidation followed by a BF 3-catalyzed Wagner Meerwein rearrangement:
5.
These include hydride shift reactions such as the Wagner-Meerwein rearrangement, where a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon.
6.
H and C NMR studies were able to confirm that any proposed Wagner-Meerwein rearrangements occurred faster than the timescale of the NMR experiment, even at low temperatures.
7.
The actual mechanism of alkyl groups moving, as in Wagner-Meerwein rearrangement, probably involves transfer of the moving alkyl group fluidly along a bond, not ionic bond-breaking and forming.
8.
With acetic acid as the solvent and with catalysis by a strong acid, alpha-pinene readily rearranges into camphene, which in turn undergoes Wagner-Meerwein rearrangement into the isobornyl cation, which is captured by acetate to give isobornyl acetate.
9.
Contrary to a carbocationic rearrangement as in the Wagner-Meerwein rearrangement in which the empty carbocationic orbital interacts positively and symmetry allowed with the filled pi orbital HOMO of the central C-C bond ( situation "'A "'in " scheme 3 " ), a filled carbanionic orbital should not be able to escape a symmetry forbidden MO overlap with the LUMO which is the empty antibonding pi orbital having one node ( situation "'B "').
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