Potassium permanganate
Manganese is also used in dihydroxylation and is often chosen when osmium tetroxide methods yield poor results. Similar to ruthenium, the oxidation potential of manganese is high, leading to over-oxidation of substrates. Potassium permanganate is often used as the oxidant for dihydroxylation; however, due to its poor solubility in organic solvent, a phase-transfer catalyst (such as benzyltriethylammonium chloride, TEBACl) is also added to increase the number of substrates for dihydroxylation.