chemchem
01-27-2009, 06:36 PM
Well I've discussed similar topics before but I thought I would focus on the first step.
A sysnthesis in the literature using Manganese dioxide as an oxidizing agent to convert codeine to 14-hydroxycodeinone and just codeinone.
A book a read tried this procedure out, took NMR's of the codeine and product to show no reaction had taken place. No signals of either oxidation.
The literature performed the reaction at room temperature, slight heating might cause the rxn to go forward. I trust that this rxn would infact work since it is published. The only possible reason might be the MnO2 used, one paper used a gamma form while the other paper just had commercial.
I was curious if anyone else is aware of a method that can oxidize allylic alcohols? Just converstion with a generic oxidizer to codeinone is also acceptable.
A sysnthesis in the literature using Manganese dioxide as an oxidizing agent to convert codeine to 14-hydroxycodeinone and just codeinone.
A book a read tried this procedure out, took NMR's of the codeine and product to show no reaction had taken place. No signals of either oxidation.
The literature performed the reaction at room temperature, slight heating might cause the rxn to go forward. I trust that this rxn would infact work since it is published. The only possible reason might be the MnO2 used, one paper used a gamma form while the other paper just had commercial.
I was curious if anyone else is aware of a method that can oxidize allylic alcohols? Just converstion with a generic oxidizer to codeinone is also acceptable.