DDTea
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1,1-Dihalo 2,2-dinitroethylene
I am interested in these, but I cannot find much information on it. The structure would look like this: (NO2)2-C=C-(X)2 . As you can see, these
would be very aggressive substances: containing 2 Nitro groups together with halogens, an unsatured C=C bond, and that all important symmetry.
The synthesis would be done from Dihaloacetylene compounds...which are extremely unstable and pyrophoric. Diiodoacetylene is the most stable of
them, the Bromide is manageable only because it is a liquid, while the Chloride is a nightmare to handle. Not only that, they are highly toxic
themselves...so for practical purposes, it would be easiest to synthesize Diiododinitroethylene:
CaC2 + I2 --> C=CI2
Now, I don't know much about adding Nitro groups, so I will leave this part up to anyone willing to help...the idea would, naturally, be to add 2
Nitro groups to the divalent Carbon. It shouldn't be terribly difficult, because in reactions that Carbon is always the "attack
point."
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Darkfire
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Admitidly i dont know much of the subject but it seems that adding the nitrates the way you sugest will be too hard to be feasible, kinda of like
solving the rubix cube one face at a time and never being able to fix that last side. It seems to me there must be another way that uses somthing
other than the c=cx2 to get ther desired product.
\"I love being alive and will be the best man I possibly can. I will take love wherever I find it and offer it to everyone who will take it. I
will seek knowledge from those wiser and teach those who wish to learn from me.\" Duane Allman
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unionised
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Against all sensible odds, nitryl chloride (NO2Cl) adds to alkynes to give the chloro nitro alkene. You can sometimes add NO2F accross a double bond
using Nitronium tetrafluoroborate in HF/ pyridine.
If those 2 reactions worked (and I bet they won't) you could convert ICCI into
INO2Cl C C INO2F
Not sure if this would be useful, but it might be interesting.
Another idea would be to start from acetylene, add NOCl2 across it to give
NO2 H C=CHCl; add alkali to remove HCl to give NO2CCH.
Repeat this to give (NO2)2 C=CH2 and then halogenate the product.
Unfortunately, there is no real hope of this working and an excellent chance of it exploding to C, N2, HCl and CO etc.
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DDTea
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What about adding straight NO2 to Diiodoacetylene? I'm thinking that it would react:
2 O2-N: + C=CI2 --> (O2N)2-C=CI2
[Edited on 4-18-04 by Samosa]
[Edited on 4-18-04 by Samosa]
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Darkfire
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Why wouldnt the double bond break open in the presence of the NO2?
[Edited on 18-4-2004 by Darkfire]
\"I love being alive and will be the best man I possibly can. I will take love wherever I find it and offer it to everyone who will take it. I
will seek knowledge from those wiser and teach those who wish to learn from me.\" Duane Allman
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unionised
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I must have missed something. Why do people keep giving a strange dihalocarbene-like structure for di halo acetylene?
I always thought they were
ICCI
ie Iodine, carbon, tripple bond, carbon, iodine.
The same as acetylene.
[Edited on 18-4-2004 by unionised]
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DDTea
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Nope, the structure isn't X-CC-X, but rather C=CX2. This is why the divalent carbon is so reactive--and why the compound is pyrophoric.
It's strange, and I thought the same thing when I first read about Dihaloacetylene compounds.
I'm sure NO2 would break the double bond if there were enough...but it would do so after bonding with the Carbon.
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Nephlite
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According to my oppinion and some reserches I can tell you that 1,1-dinitro-2,2-dihaloethylene is not existing.
I think that it's unable only one double bond to compensate the electrodeficiency of two nitro groups and two halo atoms.Maybe it's existing
for a little period of time but not in home conditions.
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DDTea
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As it turns out, this compound probably doesn't exist  . However,
1-Chloro-1-Nitroethylene does exist, though I'm not sure how it is made. It is mentioned briefly in War Gases as having "powerful"
lachrymatory properties, but not being suitable as a war gas because of its unsaturated bonds--making it prone to polymerization to non-aggressive
compounds . But ey, we're not making war gases, are we? We're
just brainstorming
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