Twistane (

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

name: tricyclo .4.0.0^3,8ecane) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...

with the formula C₁₀ H₁₆. It is a cycloalkane and an isomer of the simplest

diamondoid In chemistry, diamondoids are variants of the carbon cage molecule known as adamantane (C10H16), the smallest unit cage structure of the diamond crystal lattice. Diamondoids also known as nanodiamonds or condensed adamantanes may include one or more ...

adamantane Adamantane is an organic compound with a formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the ...

, and like adamantane, is not very volatile. Twistane was named for the way its rings are permanently forced into the

cyclohexane conformation In organic chemistry, cyclohexane conformations are any of several three-dimensional shapes adopted by molecules of cyclohexane. Because many compounds feature structurally similar six-membered rings, the structure and dynamics of cyclohexane ...

known as the "twist-boat". The compound was first reported by Whitlock in 1962.

Synthesis

Twistane has been synthesized in a variety of ways. The original 1962 method was based on a bicyclo .2.2ctane framework. A 1967 publication concerned an intramolecular

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration to ...

of a ''cis''-

decalin Decalin (decahydronaphthalene, also known as bicyclo .4.0ecane and sometimes decaline), a bicyclic organic compound, is an industrial solvent. A colorless liquid with an aromatic odor, it is used as a solvent for many resins or fuel additives. I ...

di ketone. It is formed when basketane is hydrogenated.

Symmetry

The only symmetry operation in twistane is ''rotation'', and there exist three 2-fold axes as shown in the left picture. Thus the point group of twistane is D₂. Although twistane has four

stereocenter In stereochemistry, a stereocenter of a molecule is an atom (center), axis or plane that is the focus of stereoisomerism; that is, when having at least three different groups bound to the stereocenter, interchanging any two different groups c ...

s, it only exists as two enantiomers. This is because it is symmetric along its C₂ axis.

Polytwistane

Polytwistane is a hypothetical

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

of fused twistane units awaiting actual synthesis.

References

{{Reflist, 3, refs= {{Citation , last1 =Quinkert , first1 =Gerhard , author-link = Gerhard Quinkert , last2 =Egert , first2 =Ernst , author2-link = , last3 =Griesinger , first3 =Christian , author3-link = , last4 = trans. Andrew Beard , author4-link = , publication-date = , year = 1996 , title =Aspects of Organic Chemistry: Structure , edition = , volume = , series = , publication-place = Basel, Switzerland , place = , publisher = Helvetica Chimica Acta , pages = 107 , id = , isbn =3-906390-15-2 , doi = , oclc = , url = https://books.google.com/books?id=8k0y-3MY0WgC , accessdate = 2008-12-09 {{Citation , last1 =Beyer , first1 =Hans , author-link = , last2 =Walter , first2 =Wolfgang , author2-link = , last3 = trans. Douglas Lloyd , author3-link = , publication-date = , year = 1997 , title = Organic Chemistry , edition = , volume = , series = , publication-place = , place = , publisher = Horwood Publishing , pages = 416 , id = , isbn = 1-898563-37-3 , doi = , oclc = , url = https://books.google.com/books?id=RXX2RaCplmAC , accessdate = 2008-12-09 {{Citation , last = Ho , first = Tse-Lok , author-link = , publication-date = , year = 1995 , title = Symmetry: A Basis for Synthesis Design , edition = , volume = , series = , publication-place = , place = , publisher = Wiley-IEEE , pages = 69 , id = , isbn = 0-471-57376-0 , doi = , oclc = , url = https://books.google.com/books?id=7kvAOwqRU0sC , accessdate = 2008-12-10 {{Citation , last = Kalsi , first = P. S. , author-link = , publication-date = , year = 2005 , title = Stereochemistry Conformation and Mechanism , edition = , volume = , series = , publication-place = , place = , publisher = New Age Publishers , pages = 94 , id = , isbn = 81-224-1564-4 , doi = , oclc = , url = https://books.google.com/books?id=XLWpHCMP63YC , accessdate = 2008-12-10 ''Tricyclo .4.0.03.8ecane'' H. W. Whitlock Journal of the American Chemical Society 1962 84 (17), 3412-3413 {{doi, 10.1021/ja00876a047 ''A new synthesis of twistane'' Jean Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300, {{doi, 10.1139/v67-052 ''Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives'' Henning Hopf {{ISBN, 978-3-527-29606-4. 2000 Barua, S. R., Quanz, H., Olbrich, M., Schreiner, P. R., Trauner, D. and Allen, W. D. (2014), ''Polytwistane''. Chem. Eur. J., 20: 1638–1645. {{doi, 10.1002/chem.201303081 ''A step toward polytwistane: synthesis and characterization of C2-symmetric tritwistane'' Martin Olbrich, Peter Mayer and Dirk Trauner Org. Biomol. Chem., 2014,12, 108-112 {{doi, 10.1039/C3OB42152J ''Synthetic Studies toward Polytwistane Hydrocarbon Nanorods'' Martin Olbrich, Peter Mayer, and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014 {{doi, 10.1021/jo502618g ''Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods'' Boris Maryasin, Martin Olbrich, Dirk Trauner and Christian Ochsenfeld J. Chem. Theory Comput., 2015,11(3), 1020-1026 {{doi, 10.1021/ct5011505 Polycyclic nonaromatic hydrocarbons Tricyclic compounds