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Säurekatalysierte Umlagerung von Allyl‐cyclohexadienon‐tosyl‐hydrazonen: Beispiel einer Dienimin‐Anilin‐Umlagerung
Author(s) -
Schmid [] M.,
Hansen H.J.,
Schmid H.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540402
Subject(s) - chemistry , tosyl , aniline , medicinal chemistry , yield (engineering) , sigmatropic reaction , organic chemistry , materials science , metallurgy
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.