SYNTHESIS OF 4,5-DIHYDROFURAN DERIVATIVES BY THE REACTION OF ACETYLACETONE WITH CONJUGATED ALKENES

Article abstract of DOI:10.1007/BF00557734

The reaction of the acetylacetonyl radical (generated from acetylacetone by the action of manganese acetate) with vinylacetylene, 2-vinylfuran, and butadiene was studied.The reaction proceeds nonregioselectively with vinylacetylene: 3-acetyl-2-methyl-5-ethynyl- and 3-acetyl-2-methyl-5-(4'-acetyl-5'-methyl-2'-furyl)-4,5-dihydrofurans in a ratio of 1:2.2 were isolated.The principal products in the reaction with 2-vinylfuran and butadiene were 3-acetyl-2-methyl-5-(2'furyl)- and 3-acetyl-2-methyl-5-vinyl-4,5-dihydrofurans.