Nitro-acethylen

[kemirockarfett]

What do the board think about substituting the hydrogens in C2H2 with -NO2 groups.

How to do this?

Is their any soluble acethylide salt in organic solvent their the cation could be substituted in a methastesis reaction with NO2 + ?

Boubling acethylen in nitric acid results in tetranitromethane so its not a workable idea.

The idea is to form C2(NO2)2 an explosive with perfect oxygen to carbon ratio their the tripple bounded carbon adds energy.

[Anders Hoveland]

Dinitroacetylene has never been prepared before, and if it exists it is likely to be extremely sensitive, and possibly unstable.

There are two possible methods.

Potential Method A
Dissolve anhydrous lithium nitrite in ethyl ether. Then dissolve some diiodoacetylene. For the preparation and safety of diiodoacetylene, see:
www.sciencemadness.org/talk/viewthread.php?tid=4915

"One idea would be to try reacting anhydrous lithium nitrite dissolved in ether with diiodoacetylene I--CÎC--I. One would probably want to keep the dinitroacetylene, if it forms, dissolved in the ether, otherwise it is liable to spontaneously explode."

In some of the molecules, there will also be a few nitrites stuck on in place of the nitro groups, such an arrangement is probably unstable and likely to decompose into:
ONOCCNO2 --> O=C=C(NO2)(NO)

Potential Method B
1,2-Dinitroethane can be made in good yield by reacting nitrogen dioxide with ethylene gas, at room temperature in the absence of oxygen. The dinitroethane could then be reacted with a limited quantity of sodium hypochlorite solution to add chlorine atoms onto the molecule. Ideally dichlorodinitoethane would result. It does not matter which isomer forms, so long as there are exactly 2 chlorine atoms in the molecule.

Separate out the dichlorodinitoethane from the water. Since it will be somewhat thermally unstable, distillation is not recommended. It is imparative that all the water be removed, otherwise there will be undesirable polymerization upon subsequent reaction. Dissolve in DMSO solvent, then add solid NaOH. This will pull out two HCl from the molecules, hopefully leaving dinitroacetylene. There may potentially be an explosion hazard, especially if the product is not well diluted in the solvent.


For related information, you might also see:
"Dinitroacetylene and Related Compounds"
Michael J. S. Dewar, TEXAS UNIVIVERSITY, AUSTIN.
"Only two nitroacetylenes have as yet been reported, namely isopropyl- and t-butyl-nitroacetylene, both of which were made originally by elimination of hydrogen halide from suitable precursors under rather drastic conditions. A subsidiary objective of this work was to develop new methods for preparing nitroacetylenes in general. While neither objective has been attained, the results reported here seem to have led to a better understanding of the problems involved."

www.sciencemadness.org/talk/viewthread.php?tid=259

docs.google.com/viewer?a=v&pid=explorer&chrome=true&srcid=0B9SqGkkR7PnJODlkYzAxYmYtMzJjYi00OGQ4LTllM2QtMWVhYjk5Y2I1YzY5&hl=en_US
What is most interesting about the PDF in the link, though, is his mention of a potential route to manufacture it cheaply from acetylene and a nitrating agent, forming dinitroacetylene, of which four molecules could be tetramerized to octanitrocubane, although dinitroacetylene has never yet been prepared.

Another idea would be to react NOBF4 with acetylene to make dinitrosoacetlyene, polymerize it into the cubane, then oxidize the nitroso groups to nitro using H2O2.

www.ncbi.nlm.nih.gov/pmc/articles/PMC1574367/