Journal of Organic Chemistry p. 3461 - 3464 (1980)
Update date:2022-08-04
Topics:
Snider, Barry B.
Duncia, John V.
2,6-Dimethyl-2,7-octadienal (1) undergoes a BF3-catalyzed reaction to give exo-4,8-dimethyl-2-oxabicyclo-<3.3.1>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.
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