Wagner-Meerwein Nametkin

WAGNER MEERWEIN NAMETKIN ReomngerMni Skeletal reenangement via cartxx atnns... 

WAGNER-MEERWEIN-NAMETKIN Rearrangement Skeletal rearrangement via carbocations (see 1st edition). 

Functionalization at C-9 (see Scheme 10) in camphor illustrates not only the complexity of the pathways when the possibility of Nametkin (2,3-methyl shift) and 2,6-hydride shifts are taken into account, but also one of the solutions to the simplification of the rearrangement.The product is a mixture of (-) )-and (-)-camphor-9-sulfonic acids, i.e. the pathway allows for racemization. Indeed camphor itself can be racemized in concentrated sulfuric acid by a similar pathway involving both Wagner-Meerwein and... 

This particular type of Wagner-Meerwein shift has special recognition due to its importance in the field of terpene chemistry. For example, the conversion of a-methylcamphene into 4-methylisoborneol involves both a Nametkin and a Wagner-Meerwein rearrangement. In the Meinwald rearrangement both 1,2- and 1,3-shifts occur to give different products (Scheme 2.24). 

This reaction is related to the Nametkin Rearrangement, Retropinacol Rearrangement, Tiffeneau Reaction, and Wagner-Meerwein Rearrangement. 

---