Säurekatalysierte Umlagerung von Allyl‐cyclohexadienon‐tosyl‐hydrazonen: Beispiel einer Dienimin‐Anilin‐Umlagerung
- 20 April 1971
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 54 (4) , 937-951
- https://doi.org/10.1002/hlca.19710540402
Abstract
The tosylhydrazones of 4‐allyl‐ and 4‐crotyl‐4‐methyl‐cyclohexa‐2, 5‐dien‐l‐one (14 and 15) rearrange in the presence of acid to yield the corresponding 2‐allyl‐ and 2‐α‐methylallyl‐hydrazines 17 and 18, respectively. A similar behaviour is shown by the tosylhydrazone of 2‐allyl‐2‐methyl‐cyclohexa‐3, 5‐dien‐1‐one (16). 16 could not be isolated. The observed acidcatalysed [3 s, 3 s]‐sigmatropic rearrangement of the tosylhydrazones can be regarded as a rearrangement of the dienimine‐aniline type.Keywords
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