1,3,5-Hexatriene
(Redirected from Hexatriene)
 trans-1,3,5-hexatriene | |
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3D model (JSmol) |
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| ECHA InfoCard | 100.017.082 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H8 | |
| Molar mass | 80.130 g·mol−1 |
| Appearance | yellow liquid |
| Boiling point | 80–80.5 °C (176.0–176.9 °F; 353.1–353.6 K) |
Refractive index (nD) |
1.5103–1.5119 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3,5-Hexatriene refers to a pair of organic compounds with the formula CH2=CHCH=CHCH=CH2. The compound is normally obtained as a mixture of cis- and trans-isomers.
Preparation
[edit]It can be prepared by several methods, an optimized procedure involves dehydration of 1,5-hexadiene-3-ol, which is obtained from allyl Grignard reagent and acrolein.[1]
The compound has been off interest theoretically, e.g. the Woodward-Hoffmann Rules. 1,3-cyclohexadiene undergoes photoinduced conrotatory ring-opening to give 1,3,5-hexatriene.[2]
Reactions
[edit]Protonation of 1,3,5-hexatriene gives the transient methylpentadienyl cation. It undergoes nitration, reminiscent of the behavior of benzene. With maleic anhydride, it undergoes Diels-Alder reaction.[3]
Related compounds
[edit]- Diphenylhexatriene
- 1,3,5,7-Octatetraene, a colorless solid, can be prepared by a related procedure involving pentadienal in place of acrolein.[4][5]
References
[edit]- ↑ Hwa, Jesse C. H.; Sims, Homer (1961). "1,3,5-Hexatriene". Organic Syntheses. 41: 49. doi:10.15227/orgsyn.041.0049.
- ↑ Deb, Sanghamitra; Weber, Peter M. (2011). "The Ultrafast Pathway of Photon-Induced Electrocyclic Ring-Opening Reactions: The Case of 1,3-Cyclohexadiene". Annual Review of Physical Chemistry. 62: 19–39. doi:10.1146/annurev.physchem.012809.103350. PMID 21054174.
- ↑ Woods, G. F.; Bolgiano, N. C.; Duggan, D. E. (1955). "The Chemistry of 1,3,5-Hexatriene". Journal of the American Chemical Society. 77 (7): 1800–1803. Bibcode:1955JAChS..77.1800W. doi:10.1021/ja01612a023.
- ↑ Woods, G. Forrest.; Schwartzman, Louis H. (1949). "1,3,5,7-Octatetraene". Journal of the American Chemical Society. 71 (4): 1396–1399. doi:10.1021/ja01172a073.
- ↑ Yoshida, H.; Tasumi, M. (1988). "Infrared and Raman spectra of trans,trans-1,3,5,7-octatetraene and normal-coordinate analysis based on ab initio molecular orbital calculations". The Journal of Chemical Physics. 89 (5): 2803–2809. doi:10.1063/1.454982.