Selective ortho hydroxylation of nitrobenzene with molecular oxygen catalyzed by the H5PV2Mo10O40 polyoxometalate.
Nitrobenzene was regioselectively oxidized to 2-nitrophenol with oxygen in a reaction catalyzed by the H5PV2Mo10O40 polyoxometalate. The reaction was first order in oxygen and catalyst. 15N NMR showed the interaction between nitrobenzene and the polyoxometalate. Use of labeled 18O2, H218O, a competitive kinetic isotope experiment, and use of phenyl-tert-butylnitrone as a spin-trap and identification by EPR provided evidence for formation of a radical intermediate involving a selective intramolecular interaction at the ortho position due to formation of a H5PV2Mo10O40-nitrobenzene complex.
Khenkin
Alexander M
AM
Department of Organic Chemistry and Chemical Research Support Unit, Weizmann Institute of Science, Rehovot, Israel 76100.
Weiner
Lev
L
Neumann
Ronny
R