Sciencemadness Discussion Board

modified Wohl-Aue reaction?

cumbustion - 27-8-2005 at 16:49

The wohl-aue reaction is where nitrobenzene reacts with aniline to form a substance depicted in the following link:

Wohl-Aue reaction

I was wondering if it were possible to substitute nitrobenzene with 2,4,6 trinitrobenzene and aniline with 2,4 dinitro 6 aminobenzene. Would this work? The product would be interesting.

The_Davster - 27-8-2005 at 18:37

Likely impossible with 2,4,6-trinitrobenzene and 2,4,6-trinitroaniline, but with 2,4-dinitrobenzene and 2,4-dinitroaniline it could potentially work. With the 2,4,6 trinitro compounds there is no empty sites for bonding to occur. Nitration of the end product could be interesting as well.

cumbustion - 28-8-2005 at 04:36

Whats the name for the original (unnitrated) substance? I couldn't figure it out.

cumbustion - 28-8-2005 at 04:56

Really- no room to bond? I thought there was...

modified wohl-aue.jpg - 16kB

Joeychemist - 28-8-2005 at 05:05

Quote:
Originally posted by cumbustion
Whats the name for the original (unnitrated) substance? I couldn't figure it out.


That would be Phenazine. ;)

Edit: Haha Axt, I was first :P

[Edited on 28-8-2005 by Joeychemist]

Axt - 28-8-2005 at 05:05

Quote:
Originally posted by cumbustion
Whats the name for the original (unnitrated) substance? I couldn't figure it out.


<a href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=13537156&dopt=Abstract">Phenazine</a& gt;

EDIT: Damn you joeychemist :mad: I forgot to type my password in the first time too.
Quote:
Really- no room to bond? I thought there was...


3,5-dinitroaniline has a of lot better uses then that!

[Edited on 28-8-2005 by Axt]

cumbustion - 28-8-2005 at 06:06

Would it than be a waste to start a thread on tetranitrophenazine or similar substances?
What are the exact conditions needed to bring about a wohl aue reaction? Or for that matter my modified one.
The two nitrogens in the middle of phenazine -- could they be given a positive charge and create salts in particular perchlorates?
Would that work with tetranitro phenazine as well?
Are you sure it would really be that wasteful? mad science is about exploring new substances... even IF a certain reagent is slightly impractical. Its not like were building a truck-bomb; we want to explore new energetic (and other) horizons!

:cool::cool::cool:

chemoleo - 28-8-2005 at 06:14

Well I think that's an interesting reaction.
Also, with the final product, shouldn't it be possible to form salts, i.e. nitrate or perchlorate, similar to pyridine perchlorate?

Also, reducing the bonds on the nitrogen, and subsequently forming the nitramine should make this very interesting....

But let's not turn this into a theorising thread... :)

cumbustion - 28-8-2005 at 06:22

Would it be possible to react p-dinitrobenzene with p-diaminobenzene to form long chains? Or at least p-dinitrobenzene with aniline?

Axt - 28-8-2005 at 06:31

Quote:
Originally posted by cumbustion
Are you sure it would really be that wasteful? mad science is about exploring new substances... even IF a certain reagent is slightly impractical. Its not like were building a truck-bomb; we want to explore new energetic (and other) horizons!


Im all for "explore new energetic (and other) horizons!" thats what this place is about, but no reasion to make it as impractical as possible.
3,5-dinitroaniline is the hardest to get to, nitration of aniline will result in 2,4-dinitroaniline & getting to trinitrobenzene is no easy feat.

So, the information you seek regarding nitration of phenazine should be in the article I linked to, but i dont have it. Starting with phenazine is sooo much easier then TNB/3,5-DNA which may not work at all, and the reactions involved are already documented, no guessing involved. The original article for the wohl aue reaction is on the page you first linked to "A. Wohl and W. Aue, Ber. 34, 2442 (1901)".
Quote:
Originally posted by cumbustion
Would it than be a waste to start a thread on tetranitrophenazine or similar substances?


No need to start yet another thread, just appeal to a moderator to change the title of this one to "phenazine & derivatives" or words to that effect.



[Edited on 28-8-2005 by Axt]