Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kriggy on November 29, 2018, 03:56:14 PM
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Hey guys,
im brainstorming a bit about a way how to make a dimer via N-N formation via oxidation. I know hydrazine is made this way but is this method more videly aplicable? To be more specific, I would like to make a benzimidazole dimer that is joined via the N-N bond.
I think I could make it via step by step cyclization approach but since I have the benzimidazole in lab it seems the easiest method to try
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Hypochlorite to chloramines, then Wurtz?
Err, I fear I've put nonsense, but I just couldn't resist, sorry!
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Haha thats what I was thinking but I cant find much info about those kind of reactions being applied on something else than ammonia -> hydrazine
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Grignard compound from chloramine + chloramine with catalysis ?
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And, are there already good news?
Anders Hoveland made many syntheses with unsaturated azo rings before entering the university, but he hasn't been active here for a while. Maybe you can find him on the Web, he had a website.
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Apologies, been a while since I've dropped by so missed this thread when it was active.
If you are still working on this, you might check out work by Stahl (DOI: 10.1021/jacs.8b05245) and Baran (DOI: 10.1021/ja5013323) labs in this area. If it will work with benzimidazoles though... who knows.
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Thanks for the papers, both are quite interesting. Im no longer on this though Im on one project now and we will be starting another one soon I think and this was just an random idea. I looked into the literature a bit and found some papers about the N-N linked benzimidazoles and they (and the intermediates) are bit unstable.
The Stahl procedure looks like something I could try just for fun to see if it works if I can find the correct Cu source.
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In Stahl (DOI: 10.1021/jacs.8b05245) (I access only the abstract) I don't grasp where the hydrogen shall come from to split the N-N bond
::equil:: ??
The 1atm O2 supposedly serves to consume the hydrogen atoms weakly bonded to N and provoke the N-N bonding.
Once this hydrogen is bonded to oxygen, I imagine it is irreversibly unavailable.
Do I misunderstand something?
Or could it possibly be instead that the still unbonded carbazole displaces a diphenylamine from the N-N compound, gives it a hydrogen and creates the cross-coupled N-N compound? At least the curve of species concentration versus time supports this scenario.