μ-hexacarbonyldicobalt complexes: radical cyclocondensation mediated by manganese(III) acetate
A regioselective pathway for the radical reaction of 1-alken-3-ynes with β-dicarbonyl compounds, mediated by Mn(OAc)3, can be achieved by protection of the substrate triple bond with a hexacarbonyldicobalt moiety.Dihydrofuran and hexahydrobenzofuran derivatives are formed by intermolecular oxidative cyclization of intermediate cobalt-complexed propargyl radicals.
Melikyan, Gagik G.,Vostrowsky, Otto,Bauer, Walter,Bestmann, Hans Juergen
SYNTHESIS OF 4,5-DIHYDROFURAN DERIVATIVES BY THE REACTION OF ACETYLACETONE WITH CONJUGATED ALKENES
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.
Melikyan, G. G.,Mkrtchyan, D. A.,Badanyan, Sh. O.
p. 678 - 680
(2007/10/02)
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