33834-33-2Relevant academic research and scientific papers
Electrophilic Aromatic Alkylation by Hydroperoxides. Competition between Ionic and Radical Mechanisms with Phenols
Liguori, Lucia,Bjorsvik, Hans-Rene,Fontana, Francesca,Bosco, Dino,Galimberti, Laura,Minisci, Francesco
, p. 8812 - 8815 (1999)
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 electrophilic and radical reactions with alkyl phenols. 2,2′-Dihydroxy-3,3′-di-tert-butyl-5,5′-dimethyldiphenyl is obtained in high yields from p-cresol.
