[santi prasad rath]

An Fe(II) catalyst is capable of doing alcohol oxidation in very high yield in aerobic condition at room temp with stirring in THF. So I am going to check whether it can also oxidize amines to corresponding imine (dimerized form may be) or not.
So my question is how i can isolate imine from the reaction mixture by TLC or purification process.Is silica gel GF254 (UV active) is able to detect imine from benzyl amine?
H2O is produced in situ in the reaction.Is it necessary to remove it to get imine?
neuralized silica gel (by NEt3) TLC is needed for isolating imine?
Thanks in advance.

[Dan]

neuralized silica gel (by NEt3) TLC is needed for isolating imine?

That might work, you could also try alumina instead of silica. It depends on the imine - imines from aromatic aldehydes or anilines are more stable. Oxidation of N-benzylaniline might be a good starting system to test your methodology. Another thing to consider is a trapping reagent; can you further react the imine product in the same pot to make a useful product?

[critzz]

Another thing to consider is a trapping reagent; can you further react the imine product in the same pot to make a useful product?

Yeah imines are quite tricky to analyze. I made a derivative of a piperidine-imine and it trimerized readily, and gave really nasty NMR-spectra (dependent on imine concentration and solvent). On normal TLC I had to use a MeOH/EtOAc/NH₄OH eluent to get it from the baseline. I acetylated it with Ac₂O to form the stable enamine for quantification.