Yep, the epoxide product of d9 is being formed by peroxysulfuric acid and some other reagents then catalyze a chain oxidation rxn. Idk, I know it’s happening though and it apparently works.
Edit: Chloranil is brilliant, I wanted to do this rxn with DDQ (a modern derfivative of Chloranil, but it’s was too damn expensive). I didn’t even think of Chloranil.
Chloranil
I thought the same thing. DDQ I believe is expensive and has some degree of toxicity. Supposedly 5500 times more effective than chloranil and can also be recycled back into itself. But chloranil is moderately cheap and doesn’t seem to be too toxic. The byproduct has to be disposed of properly as it is some sort of environmental hazard. It also does not seem to be able to be recycled.
Not sure how one would distill the byproduct out (Tetrachlorohydroquinone).
A modified Wacker oxidation with benzoquinone might work as well.
NASA has been reinventing the wheel for a long time and is constantly innovating. Their new titanium alloy wheels for the 2020 mars rover are looking pretty dope.
The day we stop reinventing the wheel and innovating is the day our civilization collapses.
I wish I had billions from the American tax payer.
You should not use quinones since they produce toxic byproducts. If you are comfortable with potentially ruining the market for CBN then go ahead and try this.
Also, I tried this method months ago since my graduate research involved oxidations. Chemical vendors will not let you have this molecule unless you have a good reason for it. It is considered a research chemical and must not be used in anything that will be consumed by customers. Please check the SDS for any other information.
https://www.cdhfinechemical.com/images/product/msds/37_1391757464_Chloranil-CASNO-118-75-2-MSDS.pdf
A graduate level chemist will tell you that if a procedure has been reported on a scaffold, you will use it before you start making things up. If it’s not reported for your desired scaffold, then you start to remove other functional groups to simplify the scaffold before inventing new processes.
Many reported processes work with minor adjustments. I spent 4 years figuring that out with a good range of academic projects.
Damn that is a bummer to read, was looking at this possibility, what toxic byproducts? Thanks!
You and I both know this is not true. DDQ is used in the production of many pharmaceuticals, and before they had DDQ commercially available, they used chloranil and other reagents that produce all sorts of “toxic byproducts.”
Source: https://pubs.acs.org/doi/10.1021/cr040679f
Technically no one should be consuming any of these synthetic analogues unless they’re being produced in USFDA approved manufacturing laboratories.
But here we are so I bring you all this advice:
Know your substance.
Know your source.
and…
Know your chemist.
caron2006.pdf (1.7 MB)
Out of curiosity I tried chloranil with d8 in both toluene and xylene a few weeks ago. Toluene doesn’t seem hot enough and you do see quite a bit of conversion to CBN with xylene but it’s not clean with quite a few side products that will need quite a bit of chromatography.
If your using chloranil you need to be doing a full clean up anyways
I’m making I2 today who thinks I should live feed ? Via ig for informational purposes of course 
@iLLnyeTheShatterGuy
Go live! When are you thinking
yea fudge it, I’ll watch. I liek 2 lern
I’ll be doing i2 synthesis this afternoon follow the ig my screen name with _
The paper I quoted a bit ago mentioned no reaction took place with d8 and chloranil. They stated only d9 reacted with chloranil in high yield. So it’s possible that nuking d8 as you described is what is giving your results 
. Might can try with d9 if you are curious
Toluene is nice because it’s easy for solvent recovery. Xylene is the better option because of the high bp, but you’ll deal with longer solvent recovery.
If you’re feeling cute, try to dissolve it in DMF hehe
Of course no where has the shit I need lol
I remember finding this unusual book in my first research lab. Oh the many things it can do.
https://www.amazon.com/DMF-Dimethylformamide-Chemical-R-Kittila/dp/B004V7ESNS