Chemistry Forums for Students > Organic Chemistry Forum for Graduate Students and Professionals
silylation and desilylation reviews or information
rolnor:
Great! A good end of the week.
Babcock_Hall:
We tried using TBAF on the para-isomer of our first compound (which had an ortho-relationship between the two functional groups on the aromatic ring). For some reason, the reaction failed completely. We stored the TBAF solution in the refrigerator. When we remove aliquots, we remove using a syringe. Any thoughts as to how to proceed?
rolnor:
How do you know it didnt work, NMR? If you have a hydroxy ortho to a carbonyl, deprotection may not show on TLC because you get internal hydrogen bond so Rf does not change
Babcock_Hall:
Both C-13 and H-1 NMR showed the presence of the tertiary-butyldimethylsilyl group. The product was not soluble in D2O.
rolnor:
Fluorine is so small so steric factors are small, its hard to say. Have you tried to add more reagent? As you know, its almost a fool-proof reaction.
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