[copy7]

Dear all I would like to know if it's possible to reduce -N₃  -N(NH₂)₂.

Thanks,

[discodermolide]

Dear all I would like to know if it's possible to reduce -N₃  -N(NH₂)₂.

Thanks,

I don't think so, at least not directly. Reduction of azides, at least with hydrogen, gives primary amines and nitrogen.

[copy7]

@discodermolide

Thank you for your response, could you please suggest me some indirect reaction that might be possible to do that?

[discodermolide]

@discodermolide

Thank you for your response, could you please suggest me some indirect reaction that might be possible to do that?

Not offhand, but I think you will need to go through the primary amine. It will depend on what other substituents are around.

[orgopete]

I think this is unlikely. Azide is linear and the proposed product is branched. My first question would be whether either system is known? Has anyone ever been able to prepare such a functional group? (This may be well known, but just not to me.)

Reductions of diazo compounds to hydrazines are known. I believe you can also find preparations of hydroxylamines from nitro or nitroso compounds. Obviously, these are partial reductions. Reductions to amines are probably easier to find and carry out. If one wished to do a partial reduction of an azide, you would need to contend with the potential hydrogenolysis of the intermediates.