Chemistry Forums for Students > Organic Chemistry Forum for Graduate Students and Professionals
Fluorination
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Guitarmaniac86:
I need a sense check. I have three primary alcohols in a molecule, two tertiary alcohols, an amide and a lactone.
I want to fluorinate the primary alcohols with DAST or deoxofluor but I am concerned that the tertiary alcohols will probably fluorinate. Is this actually possible? I suspect that the primary alcohols will fluorinate much faster than anything else in my molecule.
I am also trying to avoid protecting groups because I want to limit the number of steps, but I do have a route with protecting groups ready to go.
Anyone have any insights on fluorination?
phth:
The question: is the reagent a lewis acid? Is the reagent strong enough of a lewis acid to form carbocations? If the reagent does not form carbocations (check tBuOH or similar stock chem), then it's probably fine. Seems like it is worth testing.
phth:
P.S.,
Why not tosyl chloride/fluoride and pyridine?
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