meme
Harmless
Posts: 23
Registered: 2-4-2005
Member Is Offline
Mood: No Mood
|
|
Unexpected microwave hydroxylimine reaction
Recently I was attempting to dissolve hydroxylimine (CAS 90171-16-1, 10g) into a small amount of DMSO by gentle microwave heating. I have never
microwaved hydroxylimine before, but have microwaved DMSO.
In about one second a violent reaction started. The hydroxylimine got so hot as to vaporize some of the DMSO, liberated a bunch of presumably HCl
gas, and possably some dimethyl sulfide. This continued for several hours.
A google search turned up a speach entitled "Microwave Synthesis of Ketamine via a Hydroxylimine Intermediate. Lijie Yu, Health Sciences Authority,
Singapore"
Does anyone have any clue what went on? Could this have been an accidental (partial) synthesis?
EDIT S
When the product cooled, it was a solid block. The remaining DMSO softened it up to a slush over night. Adding a 15% KOH solution caused a great
deal more smoking, which lasted a minute or two. It smelled like rotting cabbage or garlic or a stinkbomb, even from a distance (I was not trying to
smell anything during this experiance).
[Edited on 13-12-2009 by meme]
|
|
|
not_important
International Hazard
Posts: 3873
Registered: 21-7-2006
Member Is Offline
Mood: No Mood
|
|
Look at the structure of your substrate, then read http://www.chem.wisc.edu/areas/reich/chem547/2-redox%7B16%7D... and finally read the first paragraph of http://en.wikipedia.org/wiki/Dimethyl_sulfide
|
|
|
meme
Harmless
Posts: 23
Registered: 2-4-2005
Member Is Offline
Mood: No Mood
|
|
So I assume that the alcohol was oxidized to the aldehyde, but any guesses as to any rearrangement? Unless I am missing something the (useful) links
posted do not help me infer what the product might be.
Hydroxylimine rearranges with at elevated temperature (180 30 minutes) but that might not be relevent here, as I don't understand the mechanism at all
but I assume the alcohol has *something* to do with it.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
