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克里格反应(Criegee reaction)指被四乙酸铅氧化,经过环状酯中间体,邻二醇的碳-碳键断裂,醇羟基转化为相应的醛、酮。反应是定量的,通常在乙酸或苯溶液中进行,可用于邻二醇的定量分析。 反应综述: 反应机理:
, The Criegee oxidation is a glycol cleavage … The Criegee oxidation is a glycol cleavage reaction in which vicinal diols are oxidized to form ketones and aldehydes using lead tetraacetate. It is analogous to the Malaprade reaction, but uses a milder oxidant. This oxidation was discovered by Rudolf Criegee and coworkers and first reported in 1931 using ethylene glycol as the substrate. The rate of the reaction is highly dependent on the relative geometric position of the two hydroxyl groups, so much so that diols that are cis on certain rings can be reacted selectively as opposed to those that are trans on them. It was heavily stressed by Criegee that the reaction must be run in anhydrous solvents, as any water present would hydrolyze the lead tetraacetate; however, subsequent publications have reported that if the rate of oxidation is faster than the rate of hydrolysis, the cleavage can be run in wet solvents or even aqueous solutions. For example, glucose, glycerol, mannitol, and xylose can all undergo a Criegee oxidation in aqueous solutions, but sucrose cannot. in aqueous solutions, but sucrose cannot.
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rdfs:comment |
The Criegee oxidation is a glycol cleavage … The Criegee oxidation is a glycol cleavage reaction in which vicinal diols are oxidized to form ketones and aldehydes using lead tetraacetate. It is analogous to the Malaprade reaction, but uses a milder oxidant. This oxidation was discovered by Rudolf Criegee and coworkers and first reported in 1931 using ethylene glycol as the substrate.31 using ethylene glycol as the substrate.
, 克里格反应(Criegee reaction)指被四乙酸铅氧化,经过环状酯中间体,邻二醇的碳-碳键断裂,醇羟基转化为相应的醛、酮。反应是定量的,通常在乙酸或苯溶液中进行,可用于邻二醇的定量分析。 反应综述: 反应机理:
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rdfs:label |
Criegee oxidation
, 克里格反应
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