Oxidation of 1 to form 2 (AS06)¶
The reaction mixture was taken off the heat and filtered through celite, before being dried with the rotary evaporator, re-dissolved in minimal DCM and left to crystallise overnight, in a dark fume hood.
Reduction of 2 to form 3 (AS05)¶
|Washing the reaction mixture in water||Precipitate falling out of hexanes:ethyl acetate (5:1)|
After the NMR showed no discernible product, I decided to continue on with the process, to see if something might pop out if we kept on purifying as per the method, so: The NMR sample was combined with the remaining dry crude from the previous step and was dissolved in minimal DCM. \(\sim\) 50 mL of hexanes:ethyl acetate (5:1) was added to the DCM and a fine white precipitate formed (subfig:AS05ppt). This was left overnight to reduce the solvent and hopefully allow the precipitate to grow into slightly larger crystals for filtering.
Maniam, S.; Sandanayake, S.; Izgorodina, E. I.; Langford, S. J. Unusual Products from Oxidation of Naphthalene Diimides. Asian J. Org. Chem. 2016, 5 (4), 490–493. https://doi.org/10.1002/ajoc.201600048. ↩