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Oxidative Cleavage of Alkynes with KMnO4

Description: Potassium permanganate (KMnO4) will cleave alkynes to give carboxylic acids.

Notes: The same reaction can be performed with ozone (O3)


Notes: Note where a terminal alkyne is being cleaved (examples 2 and 4) one of the products is carbon dioxide.

Mechanism: For the purposes of Org 1 / Org 2 the mechanism of this reaction is not considered “important”. However the first step is almost certainly the cycloaddition of MnO4 to the triple bond, followed by oxidative cleavage.