Spiropentane

Spiropentane

Names
IUPAC name Spiro[2.2]pentane
Identifiers
CAS Number	157-40-74
3D model (Jmol)	Interactive image
ChemSpider	8734
PubChem	9088
InChI InChI=1S/C5H8/c1-2-5(1)3-4-5/h1-4H2 Key: OGNAOIGAPPSUMG-UHFFFAOYSA-N
SMILES C1CC12CC2
Properties
Chemical formula	C5H8
Molar mass	68.12 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

Spiropentane is a hydrocarbon with formula C₅H₈. The simplest spiro-connected cycloalkane.^{[1][2][3][4][5]} It took several years after the discovery in 1887 until the structure of the molecule was determined.^{[6][7][8][9][10]}

References

1. Donohue, Jerry; Humphrey, George L.; Schomaker, Verner (1945). "The Structure of Spiropentane". Journal of the American Chemical Society. 67 (2): 332–335. doi:10.1021/ja01218a056. ISSN 0002-7863.
2. Applequist, Douglas E.; Fanta, George F.; Henrikson, Bertel W. (1958). "Chemistry of Spiropentane. I. An Improved Synthesis of Spiropentane". The Journal of Organic Chemistry. 23 (11): 1715–1716. doi:10.1021/jo01105a037. ISSN 0022-3263.
3. Murray, M. J.; Stevenson, Eugene H. (1944). "SPIROPENTANE". Journal of the American Chemical Society. 66 (2): 314–314. doi:10.1021/ja01230a515. ISSN 0002-7863.
4. Murray, M. J.; Stevenson, Eugene H. (1944). "The Debromination of Pentaerythrityl Bromide by Zinc. Isolation of Spiropentane1". Journal of the American Chemical Society. 66 (5): 812–816. doi:10.1021/ja01233a047. ISSN 0002-7863.
5. Price, J.E.; Coulterpark, K.A.; Masiello, T.; Nibler, J.W.; Weber, A.; Maki, A.; Blake, T.A. (2011). "High-resolution infrared spectra of spiropentane, C5H8". Journal of Molecular Spectroscopy. 269 (1): 129–136. doi:10.1016/j.jms.2011.05.011. ISSN 0022-2852.
6. Philipow, O. (1916). "Die Konstitution der Kohlenwasserstoffe Gustavsons: Vinyltrimethylen und Äthylidentrimethylen". Journal für Praktische Chemie. 93 (1): 162–182. doi:10.1002/prac.19160930112. ISSN 0021-8383.
7. Zelinsky, N. (1913). "Über das Spirocyclan, seine Synthese und sein Verhalten bei der Reduktionskatalyse". Berichte der deutschen chemischen Gesellschaft. 46 (1): 160–172. doi:10.1002/cber.19130460128. ISSN 0365-9496.
8. Fecht, H. (1907). "Über Spirocyclane". Berichte der deutschen chemischen Gesellschaft. 40 (3): 3883–3891. doi:10.1002/cber.190704003194. ISSN 0365-9496.
9. Gustavson, G. (1896). "Ueber Aethylidentrimethylen". Journal für Praktische Chemie. 54 (1): 104–107. doi:10.1002/prac.18960540106. ISSN 0021-8383.
10. Faworsky, Al.; Batalin, W. (1914). "Über das Vinyltrimethylen und Äthyliden-trimethylen von Gustavson". Berichte der deutschen chemischen Gesellschaft. 47 (2): 1648–1651. doi:10.1002/cber.19140470250. ISSN 0365-9496.