49576-27-4Relevant academic research and scientific papers
Intramolecular Diels-Alder and Ene Reactions of 2,6-Dimethyl-2,7-octadienal
Snider, Barry B.,Duncia, John V.
, p. 3461 - 3464 (2007/10/02)
2,6-Dimethyl-2,7-octadienal (1) undergoes a BF3-catalyzed reaction to give exo-4,8-dimethyl-2-oxabicyclo-non-3-ene (4) in 49percent yield.Adduct 4 is probably formed by a Lewis acid catalyzed inverse-electron-demand Diels-Alder reaction in which the α,β-unsaturated aldehyde functions as the diene.Upon pyrolysis of 1 at moderate temperatures (ca. 370 deg C), a 1:4:1 kinetically controlled mixture of Diels Alder adduct 2 and cis substituted ene adducts 14 and 15 are formed.At higher temperatures (405 deg C), complex mixtures of Diels-Alder adducts 2, 4, and 9 and ene adducts 14-18 are formed.
