18O-tracer studies of Fe(II)-induced decomposition of 1,2,4-trioxolanes (ozonides) derived from cyclopentenes and indenes.: Inner-sphere electron transfer reduction of the peroxide linkage

被引：20

作者：

Abe, M ^{[1
]}

Inakazu, T ^{[1
]}

Munakata, J ^{[1
]}

Nojima, M ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Chem Mat, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 28期

关键词：

D O I：

10.1021/ja990807v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fe(II)-induced decomposition of 1,2,4-trioxolanes (ozonides) 1 and 2 is studied in detail. The innersphere electron transfer reduction, which is sensitive to steric effects, is proposed to be a reasonable mechanism for the peroxide decomposition, i.e., the selective generation of one of the two possible Fe(III)-complexed oxy radicals. The fate of the oxy radical species is revealed in detail by using O-18-tracer studies in the reduction of O-18-labeled ozonides 1a and 2a, in which the. ethereal oxygens are labeled by O-18 atom (O-18, 77%) and also by the reduction in the presence of (H2O)-O-18 (O-18, 10%). The results of the O-18-tracer studies are consistent with the regioselective generation of the Fe(III)-complexed oxy radical species.

引用

页码：6556 / 6562

页数：7

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