ETHOXYACETYLENE: A USEFUL BUILDING BLOCK FOR THE ORGANOCOPPER(I) MEDIATED SYNTHESIS OF 1,4-DIKETONES

Article abstract of DOI:10.1016/0022-328X(86)80015-8

Ethoxyacetylene (I) has been converted by organocopper(I) species into (E)-2-ethoxy-1-alkenylcopper(I) compounds (II).The adducts II have been to shown be useful intermediates for preparation of 1,4-diketones (VI).Two routes to VI were used: (i) sequential treatment of II with allyl bromide, 3.0 N HCl, and PdCl2/CuCl in DMF/H2O, and (ii) sequential treatment of II with 2,3-dibromopropane and Hg(OAc)2.A dienone was formed from the first procedure when after the reaction of II with allyl bromide the product was treated first with the PdCl2/CuCl.