title: Electrophilic Aromatic Alkylation by Hydroperoxides. Competition between Ionic and Radical Mechanisms with Phenols.
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 TiCl(4), which is completely inactive with 2. With the latter an effective catalyst is FeCl(3), 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.
authors.affiliation: Dipartimento di Chimica del Politecnico di Milano, via Mancinelli 7, I-20131 Milano, Italy, Department of Chemistry, University of Bergen, Allégt 41, N-5007 Bergen, Norway, and Dipartimento di Ingegneria, Universitá di Bergamo, viale Marconi 5, 24044 Dalmine, BG Italy.
authors.forename: Lucia
authors.initials: L
authors.lastname: Liguori
authors.forename: Hans-René
authors.initials: HR
authors.lastname: Bjørsvik
authors.forename: Francesca
authors.initials: F
authors.lastname: Fontana
authors.forename: Dino
authors.initials: D
authors.lastname: Bosco
authors.forename: Laura
authors.initials: L
authors.lastname: Galimberti
authors.forename: Francesco
authors.initials: F
authors.lastname: Minisci