Selective ortho hydroxylation of nitrobenzene with molecular oxygen catalyzed by the H5PV2Mo10O40 polyoxometalate

被引:65
作者
Khenkin, AM
Weiner, L
Neumann, R [1 ]
机构
[1] Weizmann Inst Sci, Dept Organ Chem, IL-76100 Rehovot, Israel
[2] Weizmann Inst Sci, Chem Res Support Unit, IL-76100 Rehovot, Israel
关键词
D O I
10.1021/ja051286g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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. Copyright © 2005 American Chemical Society.
引用
收藏
页码:9988 / 9989
页数:2
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