Rearrangement studies with 14 C. XLI. Degenerate rearrangements in vinyl cations from triphenylvinyl- 2 - 14 C -phenyltriazene and from trianisylvinyl- 2 - 14 C -phenyltriazene

The triphenylvinyl cation generated from reactions of triphenylvinyl-2- 14 C-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- 14 C-phenyltriazene (2) with HOAc showed about...

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Bibliographic Details
Published in:Canadian journal of chemistry 1976-10, Vol.54 (19), p.3041-3044
Main Authors: Lee, Choi Chuck, Ko, Eric C. F.
Format: Article
Language:fre
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Summary:The triphenylvinyl cation generated from reactions of triphenylvinyl-2- 14 C-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- 14 C-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.
ISSN:0008-4042
1480-3291
DOI:10.1139/v76-431