Hydroxylamine counterparts

[moo]

After reading spric's post a little time ago swim got interested in methods for reducing nitro-compounds to hydroxylamines. There was also another post regarding catalytic hydrogenation producing hydroxylamines... This is interesting subject, because as far as swim knows, these methods would provide a whole lot of nice substances still legal in Europe, like the N-hydroxy derivatives of DOM and 2C-B to name a few.

What kind of difficulties could these hydroxylamines pose? Apparently Shulgin succeeded only in forming the oxalate salt of FLEA, for example. And what kind of yields do the mentioned methods give?

[Dr_Sister]

Moo, I just posted a ref in Low Down on Pseudonitrosites that has a compltete route to hydroxymescalin. It look a little involved, but was written long ago.

I am also very curious about its applicability to some more common rockets fuels.  Apparently the OH group reduces the toxicity of mescalin while retaining high levels of activity.

Something tells me though, it will not be as easy as swapping OHNH2 for NH3 in recipe (happy now Stoni?)

[sunlight]

I'm also interested in n-hydroxy amines. A good way could be rdxn of nitroalkene to nitroalkane, then rducing it with NH4Cl + Zn, what produces the hydroxy amine, what's your opinion ?

[Dr_Sister]

Sunlight - Not sure. Do you have a ref for the Zn reduction? I would enjoy the read.

But now that you bring it up, I vaguely remember reading about a Zn/Hg reduction() where a hydroxylamine was the by-product of a side rxn (don’t quote me though). I will look for it.

[Rhodium]

Nitroalkane => hydroxylamine refs:

JMC 31, 1960 (1988)
JOC 53, 3316 (1988) (and references therein)

http://rhodium.lycaeum.org