Sciencemadness Discussion Board

Reduction of Azines

Inorganic - 23-5-2010 at 12:55

I looking for method(without hydrides like NaBH4, LiAlH4) to reduce ketazin to N,N'-dialkylhydrazine. For example acetone azine...

Thanks in advance.

JohnWW - 23-5-2010 at 19:16

It looks as if you require a reduction that is also an hydrogenation. It could be done with some method of generating nascent (monatomic) hydrogen, to react with the ketazine. Probably the most accessible method of doing this would be reaction of Mg or Zn metal with a strong mineral acid, in the presence of the ketazine. Electrolytic generation of it at a cathode in the presence of ketazine is also possibility. Alternatively, using bottled H2, it may be possible by catalytic hydrogenation, under moderate pressure using Pd or Pt as the catalyst, or with greater pressure using finely divided Ni (Raney nickel) as the catalyst.

[Edited on 24-5-10 by JohnWW]

unionised - 24-5-2010 at 12:21

I rather suspect that strong acid would tend to hydrolyse the azine. I'd try the hydrogenation with a Pt catalyst. (actually, I'd use borohydride, but if you can't get it...)

JohnWW - 25-5-2010 at 03:22

P.S. Regarding Raney nickel for hydrogenations, see recent posts in this thread:
http://www.sciencemadness.org/talk/viewthread.php?tid=12505&...