✦ LIBER ✦
Säurekatalysierte Umlagerung von Allyl-cyclohexadienon-tosyl-hydrazonen: Beispiel einer Dienimin-Anilin-Umlagerung
✍ Scribed by M. Schmid [1]; H.-J. Hansen; H. Schmid
- Publisher
- John Wiley and Sons
- Year
- 1971
- Tongue
- German
- Weight
- 1007 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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.