Peroxidization of Naphthalene

[DONMAN]

I was wondering if a molecule such as this could exist? (click the thumb nail for a larger image).

http://img264.imageshack.us/img264/4441/peroxideoe4.th.jpg

Maybe you could convert the Naphthalene to Naphthalene tetrachloride then do a peroxidization reaction. As the potential electronegativity of the C-Cl bond is less that that of the C-O bond.

Or, would it be possible to oxidize the Naphthalene to phthalic acid and then preform the peroxidization? This would defiantly be a different molecule, but this may be the more feasible wrought...


This is probably a very KEWL question to be asking. Sorry, about that. I am looking for some books on organic peroxides but, they are kind of hard to come by.... if you have any references that would be nice.

suggestions?

[Alexires]

C-Cl 397 kJmol-1 - http://www.webelements.com/webelements/elements/text/Cl/enth.html

C-O 1076.5 kJmol-1 - http://www.webelements.com/webelements/elements/text/O/enth.html

Without consulting any of my organic chem books, I'm guessing that you could do so and that it is dependent upon the bond energy. I'm guessing that the larger the bond enthalpy, the more stable the bond?

Can someone shed light on this? I did a search for "peroxidation naphthalene", and all I could find is something relating to the peroxidation of eye lenses by naphthalene.

Not a kewl question I don't think at all donman.

[megalomania]

Eh, I can't see the thumbnail graphic, there is nothing clickable on my end...

[DONMAN]

http://img264.imageshack.us/my.php?image=peroxideoe4.jpg

Does that work for you?