Reactivity and selectivity of aryloxylium ions

AF Hegarty, JP Keogh

Index: Hegarty, Anthony F.; Keogh, Joseph P. Journal of the Chemical Society. Perkin Transactions 2, 2001 , # 5 p. 758 - 762

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Abstract

The reactivity and selectivity of aryloxylium ions in acetonitrile–water mixtures are described. The 4-bromo-2, 4, 6-trialkylcyclohexa-2, 5-dienones used as substrates were synthesised by electrophilic bromination in yields of 60%(3 R= Me) and 52%(7 R= But). Under solvolysis conditions 3 and 7 decompose cleanly via their respective aryloxylium cations to the 4- hydroxy-2, 4, 6-trialkylcyclohexa-2, 5-dienones 4 and 12. As the polarity of the solvent ...