Twistane

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Twistane
Skeletal formula Ball-and-stick model
Identifiers
CAS number 253-14-5 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H16
Molar mass 136.234 g/mol
Melting point 163-164.8°C[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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 not very volatile. Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the "twist-boat".[1]

Synthesis[edit]

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[edit]

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

References[edit]

  1. ^ a b Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd (1997), Organic Chemistry, Horwood Publishing, p. 416, ISBN 1-898563-37-3, 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, p. 107, ISBN 3-906390-15-2, retrieved 2008-12-09 
  3. ^ Ho, Tse-Lok (1995), Symmetry: A Basis for Synthesis Design, Wiley-IEEE, p. 69, ISBN 0-471-57376-0, retrieved 2008-12-10 
  4. ^ Kalsi, P. S. (2005), Stereochemistry Conformation and Mechanism, New Age Publishers, p. 94, ISBN 81-224-1564-4, retrieved 2008-12-10