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I have been wondering what this reaction would lead to? The ethyne diradical can't dimerize because triple bonded cyclic structures don't form until 8 carbons. And even if it polymerizes I find no way to end it's chain. This could probably lead to the carbyne.

Is there any literature on this out there?

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  • $\begingroup$ I'm not completely up on Kolbe mechanism, but why do you think a diradical would form? Presumably it could only form stepwise, with a mono-radical forming first. This would have to last long enough, not reacting with anything else, and be as prone to homolysis as the original non-radical carboxylate ion, to form. Not clear to me that it could. What is the Kolbe product of even a "regular" dicarboxylate like succinic acid? $\endgroup$
    – Curt F.
    Jan 22 '19 at 19:10
  • $\begingroup$ I think you are confused about the 8 carbon ring. While (E)-cyclooctene is stable. cyclodecyne is the smallest isolable cycloalkyne. In your query I believe your only source of carbon is the "diradical of acetylene". The polymerization would give a linear polyacetylene that would have to be extremely long to bite its own tail, if it could wind it. As to termination, the C-H bond dissociation energy of acetylene is 133 kcal/mol. The radical is very reactive and can abstract hydrogen from the walls of the vessel. $\endgroup$
    – user55119
    Jan 22 '19 at 22:50

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