Twistane

Twistane
IUPAC name

tricyclo[4.4.0.03,8]decane
Identifiers
CAS number 253-14-5 Y
Jmol-3D images Image 1
Properties
Molecular formula C10H16
Molar mass 136.234 g/mol
Melting point

163-164.8°C[1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Twistane (IUPAC name: tricyclo[4.4.0.03,8]decane[2]) is an organic compound with the formula C10H16. It is a cycloalkane and an isomer of the simplest diamondoid, adamantane, and like adamantane, is very volatile. Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the "twist-boat".[1]

Synthesis

Twistane has been synthesized in a variety of ways. One path is by the intramolecular aldol condensation of a cis-decalin diketone. It is formed when basketane is hydrogenated.[3]

Symmetry

Although twistane has four stereocenters, it only exists as two enantiomers. This is because it is symmetric along its C2 axis.[4]

References

  1. ^ a b Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd (1997), Organic Chemistry, Horwood Publishing, pp. 416, ISBN 1898563373, http://books.google.com/?id=RXX2RaCplmAC, retrieved 2008-12-09 
  2. ^ Quinkert, Gerhard; Egert, Ernst; Griesinger, Christian; trans. Andrew Beard (1996), Aspects of Organic Chemistry: Structure, Basel, Switzerland: Helvetica Chimica Acta, pp. 107, ISBN 3906390152, http://books.google.com/?id=8k0y-3MY0WgC, retrieved 2008-12-09 
  3. ^ Ho, Tse-Lok (1995), Symmetry: A Basis for Synthesis Design, Wiley-IEEE, pp. 69, ISBN 0471573760, http://books.google.com/?id=7kvAOwqRU0sC, retrieved 2008-12-10 
  4. ^ Kalsi, P. S. (2005), Stereochemistry Conformation and Mechanism, New Age Publishers, pp. 94, ISBN 8122415644, http://books.google.com/?id=XLWpHCMP63YC, retrieved 2008-12-10