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.

(1999). Electrophilic aromatic alkylation by hydroperoxides. Competition between ionic and radical mechanisms with phenols [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/233271

Electrophilic aromatic alkylation by hydroperoxides. Competition between ionic and radical mechanisms with phenols

Fontana, Francesca;
1999-01-01

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 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.
articolo
Liguori, Lucia; Bjorsvik, Hans-René; Fontana, Francesca; Bosco, Dino; Galimberti, Laura; Minisci, Francesco
(1999). Electrophilic aromatic alkylation by hydroperoxides. Competition between ionic and radical mechanisms with phenols [journal article - articolo]. In JOURNAL OF ORGANIC CHEMISTRY. Retrieved from https://hdl.handle.net/10446/233271
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