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Talk:Tetrahedrane

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From the article:

It is produced by decomposition of cubane (C₈H₈ → 2 C₄H₄). As there is no strain on the bonds in this molecule (being 109°), tetrahedrane is much less volatile than cubane or, indeed, many other hydrocarbons.

According to [1]: "Tetrahedrane, however, is more strained than cubane and continues to defy preparation as an isolable compound, although derivatives of the basic structure have been made.." Which seems to contradict. Maximus Rex 05:10, 20 Jul 2004 (UTC)

A series of papers in (as I recall) J.Chem.Soc. in the 1930s described a synthesis of tetrahedrane itself. I was told about it in the early 70s, but couldn't find it in Chem.Abs. - until I adopted an indirect approach. R. B. Woodward refuted it in one of his earliest papers, perhaps even while still an undergraduate; I got my lead through the Chem.Abs. author index, searching back for RBW's papers. (Hint: pyrolytic decarboxylation of tetrahedranecarboxylic acid to tetrahedrane is not going to work.)

This is one of organic chemistry's dirty little secrets, it ought to be in this article - but it needs someone with access to bound volumes to write it up.

Urban legend: RBW tracked down the perpetrator - and found him running a nightclub in New Mexico. Narky Blert (talk) 00:12, 21 February 2015 (UTC)[reply]

Hi Narky, the following citations confirm your story

• Modeling Marvels 2008, pp 81-104 Date: 05 Jun 2008 Tetrahedrane Errol G Lewars http://link.springer.com/chapter/10.1007/978-1-4020-6973-4_6
• Wiberg, Kenneth B. (1996), "Bent Bonds in Organic Compounds", Acc. Chem. Res., 29 (5): 229–34, doi:10.1021/ar950207a.

Here is a quote from the second source "In 1913, a paper by Beesley and Thorpe reported the preparation of a bicyclobutane and a tricyclobutane via elimination reactions carried out under vigorous conditions (Scheme 1).4 It is now known that even if the compounds had been formed, they would not have survived the workup conditions that were described. Bicyclobutanes undergo acidcatalyzed C-C bond cleavage at pH values as high as 4.5 A reinvestigation of the work found it to not be reproducible.6 These efforts were carried out before NMR spectroscopy and modern methods of chromatography became available, and so the identity of the products formed have not been determined, but they are probably lactones or similar compounds.7 Woodward managed to locate Beesley in Mexico working for an oil company. He informed Woodward that he had not done the work, and had been sent by Thorpe to the war because “he did not have the proper academic frame of mind”.4 It is now clear that the report is fraudulent."

But did Beesly work for a nightclub or an oil company? V8rik (talk) 19:54, 9 April 2015 (UTC)[reply]

The supposed tetrahedrane derivative was methyltetrahedranetricarboxylic acid, C₄Me(COOH)₃. Tetrahedrane itself was not actually claimed to be synthesised, IIRC.

Also, despite the name and link, a real corset does not actually work the way the tert-butyl substituents do – see Hopf, Classics in Hydrocarbon Chemistry, p. 76 (note 12). Double sharp (talk) 06:23, 23 November 2016 (UTC)[reply]

Has one ever been predicted? It might give cubane a run for the money. Double sharp (talk) 13:12, 17 September 2016 (UTC)[reply]

Cyclopropene has only 4 "H"s, whilst propene has 6, so shouldn't cyclopropene work with C? Alfa-ketosav (talk) 19:08, 30 November 2018 (UTC)[reply]