Extent of aryl rearrangement in 2-phenylethyl tosylate solvolysis

The bridged ion is apparently the stable form of the j8-phenylethyl ion in superacid media, as determined by carbon and proton NMR measurements.  

The barrier to hydride shifts in rearrangements of the r-amyl cation is 10-15 kcal/mol. This shift involves formation of a secondary ion from a tertiary one  

In the 2-butyl cation, where the hydride shift involves ions of identical energy, the activation energy is less than 6 kcal/mol. 

Although the order of migrating ability H aryl alkyl has been suggested, this 

The preferred alignment of orbitals for a 1,2-hydride or alkyl shift involves coplanarity of the p-orbital at the carbonium ion center and the orbital involved in the migration  

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Table 4.14. Extent of Aryl Rearrangement in 2-Phenylethyl Tosylate Solvolysis... 

Extent of aryl rearrangement in 2-phenylethyl tosylate solvolysis... 

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