ELECTROPHILIC HYDROXYLATION OF AROMATICS IN SUPERACIDS

Authors
JACQUESY JC BERRIER C GESSON JP JOUANNETAUD MP
Citation
Jc. Jacquesy et al., ELECTROPHILIC HYDROXYLATION OF AROMATICS IN SUPERACIDS, Bulletin de la Societe chimique de France, 131(6), 1994, pp. 658-664
Citations number
67
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
131
Issue
6
Year of publication
1994
Pages
658 - 664
Database
ISI
SICI code
0037-8968(1994)131:6<658:EHOAIS>2.0.ZU;2-9
Abstract
In superacids, protonated hydrogen peroxide hydroxylates various aroma tics to give phenols. The substrates react in their protonated forms w ith the electrophile H3O2+. Phenols (and their methyl ethers), aniline s, indolines, indoles, aromatic aldehydes and ketones are hydroxylated without any degradation; protonation protects the functional group(s) that are normally sensitive to oxidants. Electrophilic hydroxylation of polyfunctional natural products (vincadifformine, estrane derivativ es) has been successfully performed with H2O2/HF/SbF5.