Iodocubane
| Names | |
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| IUPAC name
1-iodocubane
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.459.902 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C8H7I | |
| Molar mass | 230.048 g·mol−1 |
| Hazards | |
| GHS labelling: | |
| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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Iodocubane is a chemical compound in which one hydrogen atom in the cubane molecule is replaced by iodine.
Synthesis
Iodocubane can be prepared from cubane-1,4-dicarboxylic acid via at least two routes.
The first route proceeds via esterification to the monomethyl ester, decarboxylative iodination to methyl 4-iodocubane-1-carboxylate using phenyliodine(III) diacetate,[1] followed by hydrolysis and Barton decarboxylation.[2]
The second route proceeds via decarboxylative iodination to 1,4-diiodocubane, followed by monodeiodination via metal–halogen exchange with ethylmagnesium bromide, transmetallation with n-butyllithium, and acid hydrolysis.[1]
Use
Iodocubane is employed in the synthesis of other monosubstituted cubanes.[2]
References
- ^ a b Griffiths, Justin R.; Tsanaktsidis, John; Savage, G. Paul; Priefer, Ronny (February 2010). "Thermochemical properties of iodinated cubane derivatives". Thermochimica Acta. 499 (1–2): 15–20. doi:10.1016/j.tca.2009.10.015.
- ^ a b Moriarty, Robert M.; Rao, M. (6 June 1995). "Synthesis of Cubanes and Azacubanes" (PDF). In Carrick, Patrick G.; Tam, Simon (eds.). Proceedings of the High Energy Density Matter (HEDM) Contractors' Conference held 4-7 June 1995 in Woods Hole MA (published January 1996).