89683-19-2Relevant articles and documents
HYDROXYLATION DIRECTE D'ESTERS DE PHENYLE ET D'ANILIDES PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE
Berrier, Christian,Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Morellet, Guy
, p. 158 - 164 (2007/10/02)
In SbF5-HF, hydrogen peroxide reacts on the aromatic ring of esters 1a-5a and anilides 11a-15a to give monohydroxylated derivatives in good yields.With compounds 2a, 4a and 5a, meta or para isomers are by far the major products, whereas with formate 1a and benzoate 3a, the proportion of the ortho isomer is more important.With anilides, the reaction is less selective, the three isomers being obtained in comparable amounts.Thus, the relative proportions of ortho, meta and para-hydroxylated derivatives obtained using 70 percent H2O2 with acetate 2a and acetanilide 12a are 6/51/43 and 36.5/30/33.5, respectively.The important proportion of meta hydroxylation is the result of the reaction of protonated hydrogen peroxide H3O2+ on the protonated substrate.