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Stereochemistry hydroxylation with permanganate

Hydroxylation with permanganate gives. ry/7-addition (Problem 7.11, p. 242). To account for this stereochemistry it has been suggested that an intermediate like I is involved ... [Pg.566]

Figure 10. Stereochemistry of hydroxylation reactions (1) with dilute alkaline permanganate and (2) through epoxide ring opening, (i) KMn04, NaOH (ii) m-chloroperbenzoic acid, NaHCOs, CH2Ci2 (Hi) CH3COOH (iv) base catalyzed hydrolysis. Figure 10. Stereochemistry of hydroxylation reactions (1) with dilute alkaline permanganate and (2) through epoxide ring opening, (i) KMn04, NaOH (ii) m-chloroperbenzoic acid, NaHCOs, CH2Ci2 (Hi) CH3COOH (iv) base catalyzed hydrolysis.
To hydroxylate an alkene with syn stereochemistry, which is the better reagent osmium tetroxide or potassium permanganate Osmium tetroxide gives better yields, but permanganate is cheaper and safer to use. The answer depends on the circumstances. [Pg.359]

See other pages where Stereochemistry hydroxylation with permanganate is mentioned: [Pg.162]    [Pg.3]    [Pg.227]    [Pg.1052]    [Pg.180]    [Pg.278]    [Pg.364]    [Pg.365]    [Pg.123]    [Pg.358]    [Pg.359]   


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Permanganate hydroxylation with

With permanganate

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