13154-59-1Relevant articles and documents
Reactions of 4-Hidroxycyclohexa-2,5-dienones under Acidic Conditions
Davis, Brian R.,Gash, Diana M.,Woodgate, Paul D.,Woodgate, Sheila D.
, p. 1499 - 1508 (2007/10/02)
The 4-hydroxy-4-phenyl-2,6-di-t-butylcyclohexa-2,5-dienone (2) undergoes reaction in acidic conditions to give, inter alia, derivatives of an arene-1,2-diol.In poorly nucleophilic media, the 1,1'-biphenyl-4-ol (16) and the 5-phenyl-o-benzoquinone (37) are the main products.Isolation of the 4-(2-methylpropyl)cyclohexadienone derivatives (41) and (42) provides the first examples of intermolecular trapping of a four-carbon unit.The products are consistent with the intervention of the phenoxenium ion (44); the formation of the 2-methyl-1,3-benzodioxole (43) testifies to the intermediacy of such a powerful oxidant.Whereas the 4- phenyl-2-t-butyl-p-quinol (5) gave a complex mixture from which only the 1,1'-biphenyl-4-ol derivative (24) was isolated, the 2,6-di-isopropyl- and 2,6-dimethyl-analogues (4) and (6) afforded mainly the arene-1,3-diol derivatives (48) and (47), respectively.The 4-methyl-2,6-di-t-butyl-p-quinol (7) gave products arising from nucleophilic attack on an intermediate p-quinone methide; dimers were the major products in the absence of a good nucleophile.
