Basketane

Basketane

Names
IUPAC name Pentacyclo[4.4.0.0^2,5.0^3,8.0^4,7]decane
Identifiers
CAS Number	5603-27-0
3D model (Jmol)	Interactive image
ChemSpider	16736517
InChI InChI=1S/C10H12/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h3-10H,1-2H2 Key: QKWLQWFMFQOKET-UHFFFAOYSA-N InChI=1/C10H12/c1-2-4-7-5-3(1)6-8(4)10(7)9(5)6/h3-10H,1-2H2 Key: QKWLQWFMFQOKET-UHFFFAOYAB
SMILES C2CC5C1C4C3C1C2C3C45
Properties
Chemical formula	C10H12
Molar mass	132.21 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Basketane is a polycyclic alkane with the chemical formula C₁₀H₁₂. The name is taken from its structural similarity to a basket shape.^[1] Basketane was first synthesized in 1966, independently^[2] by Masamune^[3] and Dauben and Whalen.^[4]

See also

• Cubane
• 8-Aminopentacyclo class of 'Polycyclic cage molecules'

References

1. basketane at About.com: Chemistry
2. Marchand, A. P. (1989). "Synthesis and chemistry of homocubanes, bishomocubanes, and trishomocubanes". Chem. Rev. 89 (5): 1011–1033. doi:10.1021/cr00095a004.
3. Masamune, S.; Cuts, H.; Hogben, M. G. (1966). "Strained systems. VII. Pentacyclo[4.2.2.0^2,5.0^3,8.0^4,7]deca-9-ene, basketene.". Tetrahedron Lett. 7 (10): 1017–1021. doi:10.1016/S0040-4039(00)70232-2.
4. Dauben, W. G.; Whalen, D. L. (1966). "Pentacyclo[4.4.0.0^2,5.0^3,8.0^4,7]decane and pentacyclo[4.3.0.0^2,5.0^3,8.0^4,7]nonane". Tetrahedron Lett. 7 (31): 3743–3750. doi:10.1016/S0040-4039(01)99958-7.

Further reading

• Binmore, Gavin T.; Della, Ernest W.; Elsey, G. M.; Head, N. J.; Walton, J. C. (1994). "Homolytic Reactions of Homocubane and Basketane: Rearrangement of the 9-Basketyl Radical by Multiple β-Scissions". J. Am. Chem. Soc. 116 (7): 2759–2766. doi:10.1021/ja00086a009.