Remo Galli

Nucleophilic character of alkyl radicals generated in redox processes—III : The reactivity of alkyl radicals towards conjugated olefins

Abstract New syntheses were carried out by alternating free radical additions of ethyl, n-propyl, n-butyl, sec-butyl, cyclohexyl, α-chloromethyl, α-chloroethyl, γ-chloropropyl and 5-(methoxycarbonyl) pentyl radicals to pairs of conjugated olefins. The sources of the alkyl radicals were the redox systems: acyl peroxides/cuprous ion and 1-methoxycyclohexylhydroperoxide/ferrous ion. The relative reactivities of the above mentioned radicals towards butadiene, acrylonitrile, 2,3-dimethylbutadiene, methyl acrylate, methyl methacrylate, acrylic acid and maleic anhydride are discussed in quantitative terms according to their nucleophilic character.