1,3,5-Hexatriene

1,3,5-Hexatriene.svg trans-1,3,5-hexatriene 2235-12-3 mixture of cis and trans isomers 821-07-8 E isomer 2612-46-6 Z isomer correct FDA 6WCH7CH656 218-789-7 145521 1S/C6H8/c1-3-5-6-4-2/h3,6H,1-2,5H2 KHQKGRVDIZQGHT-UHFFFAOYSA-N C=CCC=C=C 6 8 1.5103–1.5119 yellow liquid 80-80.5 1,3,5-Hexatriene refers to a pair of organic compounds with the formula CH2\dCHCH\dCHCH\dCH2. 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.1,3,5-Hexatriene Organic Syntheses 1961 41 49 10.15227/orgsyn.041.0049 free Jesse C. H. Hwa Homer Sims 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.Deb Sanghamitra Weber Peter M. The Ultrafast Pathway of Photon-Induced Electrocyclic Ring-Opening Reactions: The Case of 1,3-Cyclohexadiene Annual Review of Physical Chemistry 2011 62 19–39 10.1146/annurev.physchem.012809.103350 21054174 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.Woods G. F. Bolgiano N. C. Duggan D. E. The Chemistry of 1,3,5-Hexatriene Journal of the American Chemical Society 1955 77 7 1800–1803 10.1021/ja01612a023 1955JAChS..77.1800W Related compounds Diphenylhexatriene 1,3,5,7-Octatetraene, a colorless solid, can be prepared by a related procedure involving pentadienal in place of acrolein.Woods G. Forrest. Schwartzman Louis H. 1,3,5,7-Octatetraene Journal of the American Chemical Society 1949 71 4 1396–1399 10.1021/ja01172a073Yoshida H. Tasumi M. 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 1988 89 5 2803–2809 10.1063/1.454982 References Category:Polyenes Category:Conjugated hydrocarbons