Twistan
| Structural formula | |||||||||||||
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| General | |||||||||||||
| Surname | Twistan | ||||||||||||
| other names |
Tricyclo [4.4.0.0 3.8 ] decane ( IUPAC ) |
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| Molecular formula | C 10 H 16 | ||||||||||||
| Brief description |
Colorless crystals |
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| properties | |||||||||||||
| Molar mass | 136.23 g mol −1 | ||||||||||||
| Physical state |
firmly |
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| Melting point |
162-163 ° C |
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| safety instructions | |||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||
Twistan is an organic compound that belongs to the polycycles . The connection consists of two twisted cyclohexane rings in a boat-like structure. The name goes back to H. W. Whitlock, of which the name because of their twisted ( English : twisted ) structure.
presentation
The connection can be represented in a variety of ways. The first synthesis of Whitlock took place in 1962 starting from tricyclo [2.2.2.0 1,4 ] oct-5-en-2-acid ethyl ester within 10 synthesis steps. In 1967 a new, shorter synthesis starting from 2,7-dihydroxynaphthalene was presented.
properties
In contrast to its isomer adamantane , the compound is chiral ( axial chirality along the C 2 axis, point group D 2 ) and optically active. The specific angle of rotation for the (+) - isomer is for a concentration of 0.489 mol·l −1 in ethanol.
Individual evidence
- ↑ a b c Entry on Twistan. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2019.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ a b H.W. Whitlock: Tricyclo [4.4.0.0 3.8 ] decane . In: Journal of the American Chemical Society . tape 84 , no. September 17 , 1962, p. 3412-3413 , doi : 10.1021 / ja00876a047 .
- ↑ Jean Gauther, Pierre Deslongchamps: A new synthesis of twistane . In: Canadian Journal of Chemistry . tape 45 , no. 3 , 1967, p. 297-300 , doi : 10.1139 / v67-052 .