We really do need a chemist's couch of sorts, for shit like this, haha.
I know this is in no way practical, I am only concerned if it is
possible. I am thinking that the following procedure, although dubiously longwinded, would serve to remove one of the hardest bitches of a functional group to get off of an aromatic ring: the hydroxyl group, -OH.
The entire first row is a series of steps that all occur in the first reaction. A diazonium salt of an aromatic ring (ArN2+) attacks a phenol in the ortho position, in a standard electrophillic substitution move, forming the intermediate carbocationic ring.
By far the most stable proton to lose is the hydroxyl proton, being far more acidic than any of the protons on the ring. This gives us our compound in the topright corner.
If one could then condense this intermediate with hydrazine, one would replace the oxygen with a removable group, a nitrogen group, in theis case, a hydrazine. I show in the picture that the formed imine will rearrange to restore aromaticity, forming the phenylhydrazine, but in reality the imine is likely not an intermediate, although it does not matter in the end. The gem amino-alcohol would dehydrate not to the imine first, but likely straight to the aromatic phenylhydrazine (I think, but like I said it really doesn't matter.)
The phenylhydrazine is then oxidized with HgO or another suitable oxidant to rip off the hydrazine. The diarylazo structure is presumably immune to these type oxidants, since they are the products of the oxidation of diaryl hydrazines, ArNH-NHAr with these oxidants.
The diarylazo intermediate is then reduced with Zn/HCl to the aminobenzene/aniline. The aniline is diazotized, and reduced with Na2SO3 to the phenylhydrazine, Ph-NHNH2. This is then subjected to a second oxidation with HgO or similar catalyst to yield the free benzene.
There is no fun in reducing standard phenol to benzene, but there may be plenty fun with substituted benzenes. How's that for "novel".
PrimoPyro
Firm supporter of the "Purge The Couch!" movement. Vote for the purge today.