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A C14 tracer study of the Friedel-Crafts alkylation.

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. / Science, Faculty of / Chemistry, Department of / Graduate

Identiferoai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/40499
Date January 1956
CreatorsForman, Allan Guy
PublisherUniversity of British Columbia
Source SetsUniversity of British Columbia
LanguageEnglish
Detected LanguageEnglish
TypeText, Thesis/Dissertation
RightsFor non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.

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