The reaction of benzyl chloride with mononuclear iron pentacarbonyl quantitatively gave hydrocarbon polymer, (CH 2C 6H 4) n , n ∼ 62, and the reaction of benzyl chloride or iodobenzene with polynuclear iron carbonyls gave the corresponding symmetrical ketones. The formation of benzyl(or phenyl-)iron carbonyl (σ-complex) is considered to precede ketone formation. The reaction of benzyl chloride with polynuclear iron carbonyls in the presence of acrylonitrile (or ethyl acrylate) produce 4-phenylbutyronitrite (yield 15.0%) (or ethyl 4-phenylbutyrate, 22.2%), 4-cyano-6-phenylhexanenitrile (yield 3.3%) (or diethyl 2-β-phenethylglutarate, 4.4%) and 4-phenylcrotononitrile (1.0%). The mechanisms of these reactions are discussed.
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