[Athiril]

So I know you can form benzotriazole from o-phenylene diamine, acetic acid and sodium nitrite, but what about doing this in reverse and forming o-pd from benzotriazole as a starting material?

[orgopete]

So I know you can form benzotriazole from o-phenylene diamine, acetic acid and sodium nitrite, but what about doing this in reverse and forming o-pd from benzotriazole as a starting material?

I am guessing benzotriazole can be reduced back to o-phenylenediamine, but I am also guessing this is known. Why not look it up if you want to be sure.

[discodermolide]

I think if you heat it hard enough, flash vacuum pyrolysis, then it will eliminate nitrogen. Otherwise it is quite a stable compound.

[orgopete]

I think if you heat it hard enough, flash vacuum pyrolysis, then it will eliminate nitrogen. Otherwise it is quite a stable compound.

Benzotriazole, C6H5N3
Phenylenediamine, C6H8N2

Pyrolysis will not add the extra hydrogen atoms, except in a low yielding process? I think reduction may. Certainly one can reduce diazo compounds, nitro, nitroso, etc., so I expect reduction could work. Will it work? I think so, but it is an aromatic system and may be more resistant to reduction. Has anyone done it before? I'd start there.

[discodermolide]

I don't think it will be reducible back to ortho-phenylene diamine.

Here is a link for pyrolysis

http://www.ark.chem.ufl.edu/published_papers/pdf/013-btz.pdf

[orgopete]

I don't think it will be reducible back to ortho-phenylene diamine.

Here is a link for pyrolysis

http://www.ark.chem.ufl.edu/published_papers/pdf/013-btz.pdf

@Disco, okay you forced me to do a search. I agree that it probably won't work. Benzotriazole is a product from certain reductive reactions. If it would over-reduce, I would have expected phenylenediamine to also be a product. I didn't see any hints that was the case.

@Athiril, I'm sorry if I have provided chemical knowledge that you could have learned on your own. Although I only reported on a portion, you could have learned some chemistry by actually taking ten minutes of your time to do this search and read the results yourself. 

[Athiril]

orgopete, there is no need to be insulting, please have some manners. I spent about an hour reading but I couldn't find what I was looking for, only from going from opd to benzotriazole. Then I realised I had a forum account here, where I thought I could ask about something I'm not familiar with, and that someone might be kind enough to help, or at least put me on the right track.

[orgopete]

@athiril, sorry if I stepped on your toes. Indeed I find it frustrating that members post on the forum, "Can A be converted to B?" when both are known compounds. I do not have access to Chemical Abstracts or its equivalent. A search of CA with SciFinder would probably answer that question. Let us say a search had been done and this reaction was not found, this would have been valuable info too.