Twistane

Twistane
Names
	IUPAC name tricyclo[4.4.0.03,8]decane
Identifiers
3D model (JSmol)	Interactive image;
CompTox Dashboard (EPA)	DTXSID20420120 ;
	InChI InChI=1/C10H16/c1-2-8-6-9-3-4-10(8)5-7(1)9/h7-10H,1-6H2;
	SMILES C1CC2CC3CCC2CC13;
Properties
Chemical formula	C10H16
Molar mass	136.234 g/mol
Melting point	163-164.8°C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Twistane (IUPAC name: tricyclo[4.4.0.0^3,8]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]

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

^ ^a ^b Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd (1997), Organic Chemistry, Horwood Publishing, p. 416, ISBN 1898563373, retrieved 2008-12-09 {{citation}}: Check date values in: |accessdate= (help)
^ Quinkert, Gerhard; Egert, Ernst; Griesinger, Christian; trans. Andrew Beard (1996), Aspects of Organic Chemistry: Structure, Basel, Swtizerland: Helvetica Chimica Acta, p. 107, ISBN 3906390152, retrieved 2008-12-09 {{citation}}: Check date values in: |accessdate= (help)
^ Ho, Tse-Lok (1995), Symmetry: A Basis for Synthesis Design, Wiley-IEEE, p. 69, ISBN 0471573760, retrieved 2008-12-10 {{citation}}: Check date values in: |accessdate= (help)
^ Kalsi, P. S. (2005), Stereochemistry Conformation and Mechanism, New Age Publishers, p. 94, ISBN 8122415644, retrieved 2008-12-10 {{citation}}: Check date values in: |accessdate= (help)