Thursday, September 20, 2007

Oxidation of alcohol

several conditions and there limitations:
1. Dess-Martin
very good.
2. Swern oxidaion
gives low yield when you have an alpha-benzyl alcohol.
control temp below -65C is important for success of this rxn.
3. P2O5/DMSO
forms sticky solid in the bottle. P2O5 is very sensitive to water, hard to handle.
slightly low yield compared to swern. but works for alpha-benzyl alcohol.
5. PCC/H5IO6
very good for some substrate, ex. alpha-benzyl alcohol.
6. Jone's reagent
acidic condition, gives acid.
7. PCC/NaOAc/M.S.(1:1:1)
better work up than PCC along.

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