Iodocubane

Iodocubane
Names
IUPAC name
1-iodocubane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.459.902 Edit this at Wikidata
EC Number
  • 129-577-8
  • InChI=1S/C8H7I/c9-8-5-2-1-3(5)7(8)4(1)6(2)8/h1-7H
    Key: DEYQFBOPZRDWKH-UHFFFAOYSA-N
  • C12C3C4C1C5C2C3C45I
Properties
C8H7I
Molar mass 230.048 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
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).

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 [wd] 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

  1. ^ 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.
  2. ^ 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).

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