Coupling Reactions of 4-tert-Butyl-o-benzoquinone with Olefinic Compounds

Article abstract of DOI:10.1021/jo00248a031

Room-temperature bulk reactions of 4-tert-butyl-o-benzoquinone (5) and four alkenes, 1,4-pentadiene (6), methyl sorbate (7), methyl linoleate (8), and 3-<8'(Z),11'(E),13'(Z)-pentadecatrienyl>veratrole (9) have been studied.Reactions with methylene-interrupted olefins 6, 8, and 9 afforded C-O and C-C linked 1:1 adducts through dehydrogenation paths, whereas the cycloaddition product 13 was exclusively produced by the reaction with 7.Comparing the product distribution of these reactions and the orientations predicted by the reactivities of possible reaction species, the hydride ion transfer mechanism has been inferred to dominate in the reaction of 5 and triene 9.On the other hand, the radical path involving the transfer of a hydrogen atom has been favored for reactions of 6 and 8.