Efficient ortho-oxidation of phenols with diacyl peroxides.
A stable symmetric diacyl peroxide, m-chlorobenzoyl peroxide (mCBPO), and an asymmetric diacyl peroxide, chloroacetyl m-chlorobenzoyl peroxide (CAMCBPO), were synthesized from m-chloroperbenzoic acid. Both peroxides oxidized phenols selectively at the ortho position predominantly. CAMCBPO gave para-oxidized compounds as minor products from some phenols. The improvement of the yield of ortho-oxidation of phenols with mCBPO was also reported.
Tada
Masahiro
M
Laboratory of Bioorganic Chemistry, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, Japan. tada@cc.tuat.ac.jp
Ishiguro
Risa
R
Izumi
Ryohei
R
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D007202:Indicators and Reagents; D010545:Peroxides; D010636:Phenols