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Formatik
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Quote: Originally posted by madscientist  | ... Interestingly, it's supposedly possible to prepare HCCCl by substituting the hydroxide with potassium carbonate. Disclaimer: old references, so
who knows if it's true. Any German speakers up for some translation duty?
Chemische Berichte, 1908, vol. 41, p. 316
Chemische Berichte, 1909, vol. 42, p. 4234 |
I could take a look at it, but I can not see that what I don't have. 
| Quote: Originally posted by Anders2 | Would the reaction of diiodoacetylene with lithium nitrite in an ethyl ether solvent make dinitro-acetylene?
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I don't have references for it but, doubt it is that easy. I think the same goes for using AgNO2 instead of LiNO2, even in a solvent like pure DMSO.
Chemists have been trying to make it for many years (I think Nitrocarbons mentions something similar). Those precursors would be among first
obvious starting choices. I had also reacted DMSO solutions of AgNO2 and C2I2 a long time ago, diiodoacetylene merely precipitated and these did not
seem to react. Though I had made no effort to purify the crudely made haloalkyne, the amounts were a few milligrams, and not much more was undertaken
towards attaining a reaction. In addition to that, I didn't know what I was looking for, a vapor, solid, etc, or what the solubility is. Overall, it
wasn't a well characterized attempt, but it looks like no significant interaction took place.
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The jersey rebel
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| Quote: Originally posted by Formatik | | Quote: Originally posted by madscientist | ... Interestingly, it's supposedly possible to prepare HCCCl by substituting the hydroxide with potassium carbonate. Disclaimer: old references, so
who knows if it's true. Any German speakers up for some translation duty?
Chemische Berichte, 1908, vol. 41, p. 316
Chemische Berichte, 1909, vol. 42, p. 4234 |
I could take a look at it, but I can not see that what I don't have.
| Quote: Originally posted by Anders2 | Would the reaction of diiodoacetylene with lithium nitrite in an ethyl ether solvent make dinitro-acetylene?
|
I don't have references for it but, doubt it is that easy. I think the same goes for using AgNO2 instead of LiNO2, even in a solvent like pure DMSO.
Chemists have been trying to make it for many years (I think Nitrocarbons mentions something similar). Those precursors would be among first
obvious starting choices. I had also reacted DMSO solutions of AgNO2 and C2I2 a long time ago, diiodoacetylene merely precipitated and these did not
seem to react. Though I had made no effort to purify the crudely made haloalkyne, the amounts were a few milligrams, and not much more was undertaken
towards attaining a reaction. In addition to that, I didn't know what I was looking for, a vapor, solid, etc, or what the solubility is. Overall, it
wasn't a well characterized attempt, but it looks like no significant interaction took place. |
that may work
assuming you really keep the temp low as it’s so prone to decompose to CO2 and nitrogen gas. It would be extremely cool to make the diiodo
derivative because i could use an SN2 reaction with alkali cyanide to transform it into dicyanoacetylene
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Metacelsus
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| Quote: Originally posted by The jersey rebel | | It would be extremely cool to make the diiodo derivative because i could use an SN2 reaction with alkali cyanide to transform it into dicyanoacetylene
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Strictly speaking, alkynyl halides don't do the SN2 reaction, since backside attack isn't possible so the concerted inversion can't take place. The
mechanism for the substitution would be addition-elimination.
Copper(I) cyanide would react much more readily than an alkali cyanide, although it's possible that an alkali cyanide would work.
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The jersey rebel
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| Quote: Originally posted by Metacelsus | | Quote: Originally posted by The jersey rebel | | It would be extremely cool to make the diiodo derivative because i could use an SN2 reaction with alkali cyanide to transform it into dicyanoacetylene
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Strictly speaking, alkynyl halides don't do the SN2 reaction, since backside attack isn't possible so the concerted inversion can't take place. The
mechanism for the substitution would be addition-elimination.
Copper(I) cyanide would react much more readily than an alkali cyanide, although it's possible that an alkali cyanide would work.
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thanks for the suggestion and clarification. Still on the road to get my bachelors so still learning
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