Electrophilic Aromatic Alkylation by Hydroperoxides. Competition between Ionic and Radical Mechanisms with Phenols

L Liguori, HR Bjørsvik, F Fontana, D Bosco…

Index: Liguori, Lucia; Bjorsvik, Hans-Rene; Fontana, Francesca; Bosco, Dino; Galimberti, Laura; Minisci, Francesco Journal of Organic Chemistry, 1999 , vol. 64, # 24 p. 8812 - 8815

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Citation Number: 23

Abstract

Tertiary hydroperoxides have been utilized for the electrophilic alkylation of activated aromatic substrates, particularly phenols and phenol ethers. Cumyl (1) and tert-butyl (2) hydroperoxides have shown a greatly different behavior as concerns the catalysis and the regioselectivity. The best catalyst for 1 is TiCl4, which is completely inactive with 2. With the latter an effective catalyst is FeCl3, which, however, can give rise to a combination of ...