The rearrangements of several 2,6-di-t-butylcyclohexadienones in 9% HoSOi in acetic acid were studied. 2,6-Di-t-butyl-4-ethyl-4-methylcyclohexadien-l-one (3) gave 2-t-butyl-5-ethyl-4-methylphenol (4), which on reaction with excess bromine gave 2-t-butyl-4,6-dibromo-5-ethylphenol. 4-Allyl-2,6-di-t-butyl-4-methylcyclohexadien-l-one (7) gave a mixture of the 1,2-and 1,3rearrangement products, 3-allyl-6-t-butyl-4-methylphenol (9) and 2-al!yl-6-t-butyl-4-methylphenol (8), on treatment with acid. 4-{trans-2-ButenyT)-2,6-di-t-butyl-4-methylcyclohexadien-l-one (10) gave a mixture of 2,6-di-tbutyl-4-methylphenol and 2-(trans-2-butenyl)-6-t-butyl-4-methylphenol (12), while 2,6-di-t-butyl-4-isopropyl-4methylcyclohexadien-l-one (13) gave only 2,6-di-t-butyl-4-methylphenol in acid solution. The 1,3-rearrangements were shown to be intramolecular reactions.(1) Reactions of Cyclohexadienones. XI. Part X: B. Miller and H. Margulies, Chem. Commun. (London), 314 (1965).(2) Part of this work has been reported as a preliminary report:
Verschiedene Enolat‐Anionen (I) wurden O‐substituiert, z.B. mit (II) oder mit (IV)‐(VI), und für die verschiedenen Reaktionen wird der Einfluß von Lö= sungsmittel, Kation und Konzentration auf die verschiedenen Isomeren der Reaktionsprodukte bestimmt.
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