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The Lemieux–Johnson or Malaprade–Lemieux–Johnson oxidation is a chemical reaction in which an olefin undergoes oxidative cleavage to form two aldehyde or ketone units. The reaction is named after its inventors, Raymond Urgel Lemieux and William Summer Johnson, who published it in 1956.The reaction proceeds in a two step manner, beginning with dihydroxylation of the alkene by osmium tetroxide, followed by a Malaprade reaction to cleave the diol using periodate. Excess periodate is used to regenerate the osmium tetroxide, allowing it to be used in catalytic amounts. The Lemieux–Johnson reaction ceases at the aldehyde stage of oxidation and therefore produces the same results as ozonolysis.

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  • The Lemieux–Johnson or Malaprade–Lemieux–Johnson oxidation is a chemical reaction in which an olefin undergoes oxidative cleavage to form two aldehyde or ketone units. The reaction is named after its inventors, Raymond Urgel Lemieux and William Summer Johnson, who published it in 1956.The reaction proceeds in a two step manner, beginning with dihydroxylation of the alkene by osmium tetroxide, followed by a Malaprade reaction to cleave the diol using periodate. Excess periodate is used to regenerate the osmium tetroxide, allowing it to be used in catalytic amounts. The Lemieux–Johnson reaction ceases at the aldehyde stage of oxidation and therefore produces the same results as ozonolysis. The classical Lemieux–Johnson oxidation often generates many side products, resulting in low reaction yields; however the addition of non-nucleophilic bases, such as 2,6-lutidine, can improve on this.OsO4 may be replaced with a number of other Osmium compounds. Periodate may also be replaced with other oxidising agents, such as oxone. (en)
  • 勒米厄-约翰逊氧化反应(Lemieux-Johnson oxidation),由与在1956年报道,是将烯烃氧化为或两分子醛的方法。它分为两步。第一步为勒米厄-约翰逊试剂(高碘酸钠-四氧化锇)对烯烃的,生成邻二醇。第二步为碳-碳单键的断裂。 此反应到醛停止,不再继续氧化,总效果与烯烃臭氧化然后用还原剂处理相同。 (zh)
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  • 勒米厄-约翰逊氧化反应(Lemieux-Johnson oxidation),由与在1956年报道,是将烯烃氧化为或两分子醛的方法。它分为两步。第一步为勒米厄-约翰逊试剂(高碘酸钠-四氧化锇)对烯烃的,生成邻二醇。第二步为碳-碳单键的断裂。 此反应到醛停止,不再继续氧化,总效果与烯烃臭氧化然后用还原剂处理相同。 (zh)
  • The Lemieux–Johnson or Malaprade–Lemieux–Johnson oxidation is a chemical reaction in which an olefin undergoes oxidative cleavage to form two aldehyde or ketone units. The reaction is named after its inventors, Raymond Urgel Lemieux and William Summer Johnson, who published it in 1956.The reaction proceeds in a two step manner, beginning with dihydroxylation of the alkene by osmium tetroxide, followed by a Malaprade reaction to cleave the diol using periodate. Excess periodate is used to regenerate the osmium tetroxide, allowing it to be used in catalytic amounts. The Lemieux–Johnson reaction ceases at the aldehyde stage of oxidation and therefore produces the same results as ozonolysis. (en)
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  • Lemieux–Johnson oxidation (en)
  • 勒米厄-约翰逊氧化反应 (zh)
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