Talk:Dodecahedrane

Icosanitrododecahedrane
Imagine replacing the H with NO2 :> -- Cannibalicious!


 * Unless my intuition deceives me, octanitrocubane would be more energetic, and probably denser. The bond strain is much higher, and there's less empty space in the middle.  Also, dodecahedrane might have steric hindrance issues since there's less space between the NO2 groups.  But it would certainly be an impressive synthesis! Evand 20:16, 8 January 2007 (UTC)

Any Interest in Adding Other Approaches to Dodecahedrane?
Speaking of cubanes, Eaton took the peristylane approach to dodecahedrane. Woodward took the triquinacene dimerization approach as well as the "Weiss Reaction" approach and possibly others that show up in theses. Wender took the [2+2+2+2+2] approach. Prinzbach succeeded via the pagodane route. There are probably other routes that don't come to mind at the moment or that I never heard of (more theses). (Note: I ignore variations, such as "clamshell triquinacene", etc..) I have no idea how to submit or insert ChemDraw structures into an article. Useful addition to the main article? Not? AdderUser (talk) 02:02, 15 September 2008 (UTC)


 * It seems to me that dodecahedrane is only interesting as an exercise in synthetic chemistry; I know of no actual applications for it. Since the synthesis is the most important thing about the molecule, it seems appropriate to discuss a couple different routes.  A complete catalog of approaches should be left as a link in the references, I think, but a couple distinct routes with interesting features to them would be appropriate. Evand (talk) 03:49, 15 September 2008 (UTC)

Properties?
What are the properties of dodecahedrane? A chembox is required according to WP:MOSCHEM, and besides, I think its properties, physical or chemical, deserve at least a mention.&mdash;Tetracube (talk) 20:23, 6 July 2009 (UTC)

Icosafluorododecahedrane?
Is the perfluorinated version known? ("Icosafluorododecahedrane", right?) All the best, --Jorge Stolfi (talk) 00:06, 16 December 2009 (UTC)
 * Yup! But perfluorododecahedrane seems to be a more common name. Double sharp (talk) 05:19, 11 April 2015 (UTC)
 * P.S. Perchlorododecahedrane is also known, but only in traces (perfluorododecahedrane having been made in milligram quantities). There have been attempts to make C20Br20 and C20(OH)20 as well, but they still prove elusive. C20F20 should be very interesting due to its expected very high electron affinity, close to that of F itself. Double sharp (talk) 12:39, 19 September 2016 (UTC)

Earlier discussion limiting interest in title subject
The point taken by the earlier commentator on the Eaton effort toward dodecahedrane is apt. What modern students of OChem fail to realize is that in its time, the race to prepare dodecahedrane was quite a competition, for in that era, the synthesis of unnatural and strained molecules was receiving significant attention and funding. No, this article will not be complete without at least the description of the well-regarded and well-referenced Eaton effort (including secondary references, where, among other interesting aspects, the discovery of Lewis-acid catalyzed Diels-Alder reactions was first made and reported). Another tidbit for that eventual section. Le Prof Leprof 7272 (talk) 05:28, 5 June 2014 (UTC)

Efforts regarding total synthesis
Dodecahedrane was a well thought after target for lots of synthetic chemists. While many groups were active in - at least model studies - the honor to have taken it all the way belongs to the teams of Paquette (for being first) and Prinzbach (for developing the chemistry of dodecahedrane). In my opinion, naming other chemists has to be substantiated by suitable references to put their contribution into perspective. For example: I know that the Prinzbach team approached Paul Schleyer to test isomerization of pagodane to dodecahedrane using his method to make adamantane. The efforts led to a joint publication (and a yield for the isomerization of no more than 8% after optimization). Therefore, to name Paul as one of the main contributors to the field seems unfair to me (as much as I liked him ;) ) unless we can cite more literature. Some input to improve the introdutory section may come from Mehta cf. http://repository.ias.ac.in/29094/1/651.pdf

--Chembrainiac (talk) 08:21, 7 January 2015 (UTC)


 * Agreed, in general in articles the involved chemists are more often not named than named. Who is important and who is not? Chemists of importance tend to have a biography page. That may help the decision making V8rik (talk) 18:31, 7 January 2015 (UTC)

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