Säurekatalysierte Umlagerung von Allyl-cyclohexadienon-tosyl-hydrazonen: Beispiel einer Dienimin-Anilin-Umlagerung

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.