manimal
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Tosylhydrazide from Chloramine T?
 
Looking at these two compounds, it is apparent that the commercially available chloramine t is only an ammonia away from tosylhydrazide, a rather
useful reducing agent.
Is anyone aware if this has been done before, and if it would follow the general paradigm of the classical chloramine hydrazine synthesis?
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AndersHoveland
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It might not work. If you consider the reaction mechanism for how chloramine reacts with ammonia, the charge distribution here could interfere.*
The extra negative electric charge would actually be resonating around, the oxygen atoms likely have more charge distribution than the nitrogen atom.
What would likely happen is that hypochlorous acid would simply hydrolyze off Chloramine T (in equilibrium), oxidize the free ammonia, and you would
only get regular N2H4 at best.
( I made a post with some more detail about this, Fourteenth post down here: http://www.sciencemadness.org/talk/viewthread.php?tid=25005 )
[Edited on 27-8-2013 by AndersHoveland]
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