[amintobello]

Hi everyone i want to ask about a reaction.I formulated a reaction but i couldn't find any information.Here is reaction:
First step:
http://imageshack.us/photo/my-images/259/82077189.jpg/
Second step:
http://imageshack.us/photo/my-images/80/26877032.jpg/

Reaction continues like that.So here is questions:
1.)Does any chemicals needed to start reaction?(If so what can be used?)
2.)As most of us know peroxides are not very stable structures will it cause serious problems?(Decomposition before use for anything etc.)
3.)I guess it will be very sensitive explosive if so is it usable in any purpose?

[Honclbrif]

I think there's a reason you didn't find any information on this reaction and furthermore would recommend never trying it.

[amintobello]

What kind of reason did you think?

[Arctic-Nation]

Apart from attempting a nucleophilic aromatic substitution on an unactivated benzene derivative? You're basically trying to recreate the Dow phenol process with peroxides. Think about it.

[amintobello]

I could not understand smiliarity between dow phenol process and this reaction.I thought it has to be work like this reaction:

[Honclbrif]

If you don't mind me asking, why do you even want this peroxide polymer in the first place? It seems like it would be unstable and hazardous.

[amintobello]

I don't want this polymer i want to see is it true what did i think.

[nox]

If we assume the S_NAr reaction somehow works, the thing will explode in your face long before it polymerizes to any extent.

[Vidya]

This reaction will not take place and in case it is forced to take place by making reaction conditions tough this will result in breakdown of the sodium peroxide reagent

[Honclbrif]

Ok, I'm fairly sure you won't go out and try to make this stuff (If i hear on the news tomorrow you tried this and blew up your face I will be very upset). The usual way for functional groups to be added to an aromatic ring is via electrophilic substitution. I hope I don't have to explain the mechanism to you. What you are proposing is nucleophilic aromatic substitution, which is a totally different animal. It works best when there's an pi-withdrawing group ortho or para to the leaving group (again, draw out the mechanism and it will make perfect sense). In this case you've got a chloride para to the leaving group. Since chloride is a pi-donating group, I would suspect that this particular reaction would be disfavored.

You've thrown up some sort of example (without reference) involving sulfides. Sulfide is a pretty badass nucleophile, so I would suspect it might be able to "throw its weight around" better than other nucleophiles. Don't get me wrong, peroxide is pretty good too, but its not as polarizable. Honestly, I don't think this reaction would work (or would at best produce oligomers), but I'm not 100% on that. The best way to tell would be to do it but that would, as has been previously mentioned, probably result in nothing or explodey death.

[opsomath]

Yeah, the conditions for forcing out Cl- leaving group on an unactivated aryl ring would decompose peroxide in no time flat.

Who knows, it might even be possible if you use an activated ring system, such as 1,4-dicarboxy-2,4-dichlorobenzene diethyl ester.

[amintobello]

Thanks for every answer and Honclbrif sorry about forgetting reference sodium sulfide reaction from wikipedia p-dichlorobenzene page
http://en.wikipedia.org/wiki/P-dichlorobenzene#Precursor_to_other_chemicals
Thanks everyone again

[Honclbrif]

opsomath : "Who knows, it might even be possible if you use an activated ring system, such as 1,4-dicarboxy-2,4-dichlorobenzene diethyl ester."

Can you imagine how awesome the analogous compound from 1,4-dichloro-2,5-dinitrobenzene would be? Don't sneeze, don't even look at it!

[opsomath]

I've got a better one. What's the best leaving group in the world? Diazonium. How about 1,4-bisdiazonium-2,5-dinitrobenzene perchlorate?

[Honclbrif]

I think part of the internet exploded from you just typing that. Lets throw in some peroxide, heat 'er to reflux, and update our wills.