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It took several years after the discovery in 1887 until the structure of the molecule was determined.<ref name="Philipow1916">{{cite journal|last1=Philipow|first1=O.|title=Die Konstitution der Kohlenwasserstoffe Gustavsons: Vinyltrimethylen und �thylidentrimethylen|journal=Journal f�r Praktische Chemie|volume=93|issue=1|year=1916|pages=162–182|issn=0021-8383|doi=10.1002/prac.19160930112}}</ref><ref name="Zelinsky1913">{{cite journal|last1=Zelinsky|first1=N.|title=Über das Spirocyclan, seine Synthese und sein Verhalten bei der Reduktionskatalyse|journal=Berichte der deutschen chemischen Gesellschaft|volume=46|issue=1|year=1913|pages=160–172|issn=03659496|doi=10.1002/cber.19130460128}}</ref><ref name="Fecht1907">{{cite journal|last1=Fecht|first1=H.|title=Über Spirocyclane|journal=Berichte der deutschen chemischen Gesellschaft|volume=40|issue=3|year=1907|pages=3883–3891|issn=03659496|doi=10.1002/cber.190704003194}}</ref><ref name="Gustavson1896">{{cite journal|last1=Gustavson|first1=G.|title=Ueber Aethylidentrimethylen|journal=Journal f�r Praktische Chemie|volume=54|issue=1|year=1896|pages=104–107|issn=0021-8383|doi=10.1002/prac.18960540106}}</ref><ref name="FaworskyBatalin1914">{{cite journal|last1=Faworsky|first1=Al.|last2=Batalin|first2=W.|title=Über das Vinyltrimethylen und Äthyliden-trimethylen von Gustavson|journal=Berichte der deutschen chemischen Gesellschaft|volume=47|issue=2|year=1914|pages=1648–1651|issn=03659496|doi=10.1002/cber.19140470250}}</ref>
It took several years after the discovery in 1887 until the structure of the molecule was determined.<ref name="Philipow1916">{{cite journal|last1=Philipow|first1=O.|title=Die Konstitution der Kohlenwasserstoffe Gustavsons: Vinyltrimethylen und �thylidentrimethylen|journal=Journal f�r Praktische Chemie|volume=93|issue=1|year=1916|pages=162–182|issn=0021-8383|doi=10.1002/prac.19160930112}}</ref><ref name="Zelinsky1913">{{cite journal|last1=Zelinsky|first1=N.|title=Über das Spirocyclan, seine Synthese und sein Verhalten bei der Reduktionskatalyse|journal=Berichte der deutschen chemischen Gesellschaft|volume=46|issue=1|year=1913|pages=160–172|issn=03659496|doi=10.1002/cber.19130460128}}</ref><ref name="Fecht1907">{{cite journal|last1=Fecht|first1=H.|title=Über Spirocyclane|journal=Berichte der deutschen chemischen Gesellschaft|volume=40|issue=3|year=1907|pages=3883–3891|issn=03659496|doi=10.1002/cber.190704003194}}</ref><ref name="Gustavson1896">{{cite journal|last1=Gustavson|first1=G.|title=Ueber Aethylidentrimethylen|journal=Journal f�r Praktische Chemie|volume=54|issue=1|year=1896|pages=104–107|issn=0021-8383|doi=10.1002/prac.18960540106}}</ref><ref name="FaworskyBatalin1914">{{cite journal|last1=Faworsky|first1=Al.|last2=Batalin|first2=W.|title=Über das Vinyltrimethylen und Äthyliden-trimethylen von Gustavson|journal=Berichte der deutschen chemischen Gesellschaft|volume=47|issue=2|year=1914|pages=1648–1651|issn=03659496|doi=10.1002/cber.19140470250}}</ref>


<!--==Synthesis==


After Gustavson had produced [[cyclopropane]] by reacting 1,3-dibrompropane with dust fine zinc, he tried the same reaction with 2,2-Bis(brommethyl)-1,3-dibrompropane. The compound is easiely obtain by reacting [[pentaerytrit]] with [[hydrobromic acid]]. He obtain a molecule with the formula C<sub>5</sub>H<sub>8</sub> he first thought to be a vinyltrimethylene

-->
==References==
==References==
{{reflist}}
{{reflist}}

Revision as of 22:20, 4 November 2015

Spiropentane
Names
IUPAC name
Spiro[2.2]pentane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H8/c1-2-5(1)3-4-5/h1-4H2
    Key: OGNAOIGAPPSUMG-UHFFFAOYSA-N
  • C1CC12CC2
Properties
C5H8
Molar mass 68.119 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 �thylidentrimethylen". Journal f�r Praktische Chemie. 93 (1): 162–182. doi:10.1002/prac.19160930112. ISSN 0021-8383. {{cite journal}}: replacement character in |journal= at position 10 (help); replacement character in |title= at position 74 (help)
  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 f�r Praktische Chemie. 54 (1): 104–107. doi:10.1002/prac.18960540106. ISSN 0021-8383. {{cite journal}}: replacement character in |journal= at position 10 (help)
  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.
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