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Alkene reactivity

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sjb:

--- Quote from: rolnor on February 19, 2023, 01:20:38 PM ---Its a chiral product so you need to do asymetric dihydroxylation.

https://en.wikipedia.org/wiki/Sharpless_asymmetric_dihydroxylation

--- End quote ---

True - but it might just be referring to the Z diastereomeric pair.

rolnor:
As the structure of the compound is drawn, its chiral. It can be non-correctly drawn, yes. I think OsO4 will hydroxylate double-bonds in the body and be re-oxidized so even small amounts will hurt the biology inj the body. Compounds like phosghene will be consumed and will be neutralized in the body, its not catalytical. Many toxic things in nature are enzymes, Botuline and many snake-venoms are enzymes and they catalyticaly interfere with the biochemistry. I have worked a lot with OsO4 and its volatile, you get it in the rotavapor solvent waste, you get it everywhere. Not very nice.

Babcock_Hall:
There is a method that uses NMO (the N-oxidized form of N-methylmorpholine) as the oxidant, with OsO4 as the catalyst.  My inference is that using NMO is a safer alternative to using stoichiometric OsO4.

rolnor:
OsO4 is expensive and toxic so deffinetly use it catalytic.

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