Phase-vanishing methodology for efficient bromination, alkylation, epoxidation, and oxidation reactions of organic substrates

Phase-vanishing methodology for efficient bromination, alkylation, epoxidation, and oxidation reactions of organic substrates
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DOI:
10.1021/ol035391b
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发表时间:
2003-10-16
期刊:
影响因子:
5.2
通讯作者:
Verkade, JG
Verkade, JG
中科院分区:
化学1区
文献类型:
--
作者:
Jana, NK;Verkade, JG

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在相消失反应中的两种反应物的密度都小于氟相的情况下,U管法的替代方法是使用密度比氟相更大的溶剂,如1,2-二溴乙烷。这一修饰已成功地应用于苯酚衍生物与硫酸二甲酯的甲基化反应、间CPBA引发的烯烃环氧化反应、含氮化合物生成N-氧化物的反应以及由有机硫化物生成S氧化物或砜的反应。
[GRAPHICS]In cases where both reactants in a phase-vanishing reaction are less dense than the fluorous phase, an alternative to the U-tube method is to employ a solvent with greater density than the fluorous phase, such as 1,2-dibromoethane. This modification has been successfully applied to the methylation of a phenol derivative with dimethyl sulfate and to the m-CPBA-induced epoxidation of alkenes, N-oxide formation from nitrogen-containing compounds, and S-oxide or sulfone formation from organic sulfides.