I have tried using DDQ to aromatize a compound and the work up was a disaster. I'd appreciate any tips about safety and work up with this material from someone who has used it. I used 1.1 equivalents and refluxed with my starting material in dry dioxane. Should I quench the reaction with aqueous sodium bisulfite or is that not necessary? Is there really such a big risk or cyanide formation?
What color is DDQ-H? I can't find any references about it. Anyway, I added water and got a red precipitate. My compound is new but I am expecting it to be colored and also insoluble in some solvents. I filtered and rinsed with aq bicarb, thinking any DDQ-H would rinse out and got a bright yellow filtrate and the red stuff remained. So could the red solid be my product or is it trapped in the red stuff which is the DDQ-H? I tried to take an NMR of the red solid and it was too messy to be helpful.