Alkene Oxidations using KMnO4

Alkene Oxidations using KMnO4 - Oxidation by permanganate:...

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Mn O O O O O Mn O O O H + , H 2 O, Heat O OH O HO + MnO 2 (s) Mn O O O O O Mn O O O + MnO 2 (s) NaOH, H 2 O HO OH Alkene Oxidations using KMnO 4 Oxidative Cleavage using concentrated KMnO 4 Syn Diol Formation using dilute KMnO 4 (1-4%) “Permanganate is a versatile oxidizing agent and is used for studying the oxidation kinetics of many organic substrates. The mechanisms for different organic substrates suggested by various authors are not similar, indicating that a variety of mechanisms are possible, depending upon the nature of the reactive manganese species, the reaction environment and the nature of the substrate…Owing to the rapidity and the complex mechanism of the permanganate oxidations, the mechanisms of oxidation of various [alkene] derivatives are still poorly understood.”
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Unformatted text preview: Oxidation by permanganate: synthetic and mechanistic aspects, Sukalyan Dash, Sabita Patel, Bijay K. Mishra, Tetrahedron , 2008 + HBr N O O Br + Br 2 N O O H Br 2 light 2 Br C C C H H + Br 2 C C C H H Br + Br Trace Low Concentration CCl 4 C C C H H H + Br C C C H H + HBr C C C H H C C C H H Note: This radical is stablized by resonance N-bromosuccinimide Mechanism of Allylic Halogenation using N-bromosuccinimide (NBS) C C C C O 3 C C C C O O O C C O O O C C C C O O O C C C O O C C O C C O O C O O C O C C C H 3 C S CH 3 O C O C C C H 3 C S CH 3 O Zwitterion Resonance Unstable Molonozide Stable Ozonide Cycloaddition Cycloreversion Mechanism of Ozonolysis...
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Alkene Oxidations using KMnO4 - Oxidation by permanganate:...

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