3-Phenyl-2-butyl-tosylate acetolysis

An interesting example of this type has been provided by Cram/ who studied the rates of acetolysis of optically active 3-phenyl-2-butyl tosylate in glacial acetic acid ... 

Figure 28.7. Acetolysis of racemic 3-phenyl-2-butyl tosylates.

In the controversy that developed, the point under attack was not so much the existence of the intermediate bridged ion—although this was questioned, too— as its mode of formation. The 3-phenyl-2-butyl tosylates undergo solvolysis at much the same rate as does unsubstituted e c-butyl tosylate formolysis a little faster, acetolysis a little slower. Yet, as depicted by Cram, phenyl gives anchimeric assistance to the reaction. Why, then, is there no rate acceleration ... 

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