Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
Author: Subject: Substituting hydrogens in hydroxylamine
Eddygp
International Hazard
*****




Posts: 858
Registered: 31-3-2012
Location: University of York, UK
Member Is Offline

Mood: Organometallic

[*] posted on 15-9-2013 at 13:04
Substituting hydrogens in hydroxylamine


I had been thinking for a while about hydroxylamine, NH2OH, and about the possibility of substituting the amine's hydrogens (not the hydroxyl one) by any R group. This would yield things like N(CH3)2OH or, in general, NRR'(OH). EDIT: Not ketoximes, because I don't want to use that carbon double bond to the nitrogen!!
I would like to see if it would be easy to do so from scratch, or with techniques available to home chemists (that is, not using a palladium catalyst heated up at 820K under 2.3 atm of pressure).
Just curious about it.
EDIT: Uploaded an image of a possible compound:

[Edited on 15-9-2013 by Eddygp]

truc.jpg - 20kB




there may be bugs in gfind

[ˌɛdidʒiˈpiː] IPA pronunciation for my Username
View user's profile View All Posts By User
AndersHoveland
Hazard to Other Members, due to repeated speculation and posting of untested highly dangerous procedures!
*****




Posts: 1986
Registered: 2-3-2011
Member Is Offline

Mood: No Mood

[*] posted on 15-9-2013 at 21:17


I have previously been thinking about the easiest routes to N,N-dimethyl hydroxylamine, because I think it could form very stable and very powerful explosive salts (particularly the nitroformate).

Would bromomethane add methyl groups to hydroxylamine? If the hydroxyl group got methylated, could that not just afterwards be hydrolyzed off with acid?

Typically the routes to hydroxylamine derivatives do not start with hydroxylamine.

One lab preparation I saw was oxidation of N,N-dimethyl-cyclohexylmethylamine with H2O2 to the N-oxide, then pyrolysis at 160 C, releasing the dimethylhydroxylamine, and leaving an unsaturated methylenecyclohexane.
View user's profile Visit user's homepage View All Posts By User
Eddygp
International Hazard
*****




Posts: 858
Registered: 31-3-2012
Location: University of York, UK
Member Is Offline

Mood: Organometallic

[*] posted on 19-9-2013 at 12:40


Beg my scarce and sparse knowledge, but I think that the bromomethane would probably alkylate the hydroxyl group instead.



there may be bugs in gfind

[ˌɛdidʒiˈpiː] IPA pronunciation for my Username
View user's profile View All Posts By User
DraconicAcid
International Hazard
*****




Posts: 3950
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Offline

Mood: Semi-victorious.

[*] posted on 19-9-2013 at 13:49


Quote: Originally posted by Eddygp  
Beg my scarce and sparse knowledge, but I think that the bromomethane would probably alkylate the hydroxyl group instead.


Not sure about that- nitrogen tends to be a better nucleophile than oxygen.




Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
View user's profile View All Posts By User
Eddygp
International Hazard
*****




Posts: 858
Registered: 31-3-2012
Location: University of York, UK
Member Is Offline

Mood: Organometallic

[*] posted on 21-9-2013 at 00:27


Oh, my bad! That is true, DraconicAcid! However, it might not react evenly giving either N,N-dimethylhydroxylamine or N-methylhydroxylamine... even with stoichiometric proportions it would reach at a certain point an equilibrium. A catalyst or a temp. change would be needed then, drawing the equilibrium to the product. After that something should be added to react with the hydroxylamine but not with the product.



there may be bugs in gfind

[ˌɛdidʒiˈpiː] IPA pronunciation for my Username
View user's profile View All Posts By User

  Go To Top