Synthetic aspects of free radical addition reactions. Part V. Alkylation of compounds containing activated methylene and methine groups

Abstract

Free-radical induced addition reactions of oct-1-ene and the following compounds containing activated methylene or methine groups have been effected: diethyl butylmalonate, di-isopropyl malonate, diethyl acetylmalonate, diethyl cyanomalonate, triethoxycarbonylmethane, 1,1,2-triethoxycarbonylethane, ethyl diacetylacetate, and ethyl phenylacetate. The radical-induced additions of ethyl acetoacetate and diethyl ethylmalonate, and the peroxide- and photo-induced reactions of acetylacetone, with oct-1-ene have been re-investigated. The synthetical and theoretical consequences of these reactions and the possible significance of the degree of enolisation of certain of the addenda with respect to the nature of the products are discussed.