Abstract
The triphenylvinyl cation generated from reactions of triphenylvinyl-2-14C-phenyltriazene (1) with a number of acids gave no isotopic scrambling from degenerate 1,2-phenyl shifts. The trianisylvinyl cation generated from reaction of trianisylvinyl-2-14C-phenyltriazene (2) with HOAc showed about 38% scrambling of the label from C-2 to C-1, attributable to degenerate 1,2-anisyl shifts. When 2 was treated with HOAc containing 1.7 equiv. of NaOAc, the extent of scrambling was decreased to about 17%. Mechanistic implications of these results are discussed.
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