MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .107. CATALYTIC-OXIDATION OF PARTIALLY AND FULLY FLUORINATED OLEFINS WITH OSMIUM-TETROXIDE

MULTIPLE BONDS BETWEEN MAIN-GROUP ELEMENTS AND TRANSITION-METALS .107. CATALYTIC-OXIDATION OF PARTIALLY AND FULLY FLUORINATED OLEFINS WITH OSMIUM-TETROXIDE
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DOI:
10.1002/anie.199213451
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发表时间:
1992-10-01
期刊:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH
影响因子:
--
通讯作者:
SCHERER, W
SCHERER, W
中科院分区:
其他
文献类型:
--
作者:
HERRMANN, WA;EDER, SJ;SCHERER, W

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一个普遍持有的概念最容易被修改。由于假设贫电子的烯烃不会与OsO4发生反应,所以从未用氟化烯测试过OsO4催化的烯烃顺式羟基化反应。但在标准反应条件下,即使是全氟烯烃也能快速、定量地转化为1,2,4,4,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,6,5,6,6,6,6,6,6,6,6,6,6,5,6,6,5,5,6-三甲氧基-1,4,4,4,4,4,4,4,4,4,4,4,4,6,6,6,6,4,4,4,4,4,4,4,4,4,4,4,4,4,4,4,4,4,它们随后的水解生成顺式二醇、酮或1,2-二酮。
A commonly held conception most be revised. The OsO4-catalyzed cis-hydroxylation of olefins was never tested with fluorinated olefins, because it was assumed the electron-poor olefins would not react with OsO4. But under the standard reaction conditions even perfluorinated olefins can be converted into osmate esters such as 1 quickly and quantitatively. Their subsequent hydrolysis provides cis-diols, ketones, or 1,2-diketones.