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A C14 tracer study of the Friedel-Crafts alkylation. Forman, Allan Guy


Anisole was alkylated with 2-phenylethanol-1-C¹⁴ and 2-phenylethyl-1-C¹⁴ chloride respectively, using aluminum chloride as catalyst, to give p-methoxydibenzyl. Radioactivity assay of the p-methoxydibenzyl and of the anisic acid obtained by oxidative degradation with alkaline permanganate showed that a 50% rearrangement of C¹⁴ from the C-1 to C-2 positions occurred with both alkylating agents. The reaction may proceed by means of electrophilic attack of a free carbonium ion, or by a nucleophilic attack of anisole on a polarized complex between the alkylating agent and catalyst, if it may be assumed that the observed rearrangement has taken place during the formation of the polarized complex. The possibility exists that the rearrangement may arise from a process separate from the alkylatlon reaction itself.

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