December 20, 2024, 07:09:45 PM
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Topic: synthesis of cubane  (Read 31988 times)

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Offline Enthalpy

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Re: synthesis of cubane
« Reply #30 on: February 10, 2022, 07:56:39 AM »
Cyclooctatetraene (COT) is mass-produced by tetramerization of acetylene over a catalyst. It has its atoms more distant but arranged similarly to ladderdiene and cubane, so high pressure might perhaps synthesize ladderdiene or cubane by reorganising the electrons, with the optional help of light as from ethylene to cyclobutane.

A laboratory diamond anvil would produce tiny amounts, but if this path works, it can be hugely accelerated, maybe scaled up too.

Marc Schaefer, aka Enthalpy

Offline rolnor

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Re: synthesis of cubane
« Reply #31 on: February 10, 2022, 09:47:36 AM »
Tetraazacubane would be sexy.   But instead of methyls I would prefer NO2 groups  ;D
tetranitrotetraazacubane tetroxide C4N8O12.... use it as the oxidizer with the tetramethyl stuff  ;)

The fact that it has not been prepared would make me think it is rather more difficult than the corrresponding cubane.

If you have nitrogens with just one carbon between, this would be a aminal and perhaps not so stable. I know of hexamethylenetetramine that you can make from formaldehyde and ammonia.

Offline Enthalpy

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Re: synthesis of cubane
« Reply #32 on: February 11, 2022, 05:53:25 PM »
Hi Rolnor and everybody, nice to read you again!

Yes, we had a discussion there about geminal amines
https://www.chemicalforums.com/index.php?topic=46407.0
including urea-formaldehyde polycondensate and many more. Tertiary amines seem to be more stable, but double bonds help too, which led me imagine that NH3 evolution might be what limits the life of geminal amines.

Offline rolnor

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Re: synthesis of cubane
« Reply #33 on: February 13, 2022, 12:26:05 PM »
Nice to read your posts also Enthalpy!

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