Abstract
a Conditions: Aromatic substrate/MX3/AH=1/0.05/0.1 molar ratio except for entry 10 where this ratio is 1/0.1/0.2 and entries 11 and 12 where this ratio is 1/0.2/0.4. Reactions carried out at 100°C using toluene as the solvent (c=0.867 M relative to the aromatic substrate) except for entries; aromatic substrates: naphthyl acetate (1a), naphthyl hexanoate (2a), naphthyl isobutyrate (3a), naphthyl cyclohexylcarboxylate (4a), naphthyl benzoate (5a), 3-methoxy-1-phenyl acetate (6a), 3-methyl-1-phenyl acetate (7a). b Products: 1-hydroxy-2-naphthyl pentyl ketone (2b), 1-hydroxy-2-naphthyl isopropyl ketone (3b), 1-hydroxy-2-naphthyl cyclohexyl ketone (4b), 1-hydroxy-2-naphthyl phenyl ketone (5b), 2-hydroxy-4-methoxyphenyl methyl ketone (6b), 2-hydroxy-4-methylphenyl methyl ketone (7b). c Only traces of 1b were obtained under the same conditions when Y(NTf2)3 was used alone. d No reaction occurred under the same conditions when Y(OMs)3 was used alone. e This experiment has been carried out at 150°C using 4-chlorotoluene instead of toluene. f This experiment has been carried out in nitroethane instead of toluene and gave a similar yield. g Containing 4-hydroxy-2-methoxyphenyl methyl ketone (yield 7%).
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