1,3,5-Hexatriene

1,3,5-Hexatriene
trans-1,3,5-hexatriene
Identifiers
3D model (JSmol)
ECHA InfoCard 100.017.082 Edit this at Wikidata
EC Number
  • 218-789-7
UNII
  • InChI=1S/C6H8/c1-3-5-6-4-2/h3,6H,1-2,5H2
    Key: KHQKGRVDIZQGHT-UHFFFAOYSA-N
  • C=CCC=C=C
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)
1.5103–1.5119
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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.

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.

Reactions

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.

References

  1. ↑ Hwa, Jesse C. H.; Sims, Homer (1961). "1,3,5-Hexatriene". Organic Syntheses. 41: 49. doi:10.15227/orgsyn.041.0049.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.