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  • The "kinetic capture" of an acylium ion from live aluminum chloride promoted Friedel-Crafts acylation reactions.

The "kinetic capture" of an acylium ion from live aluminum chloride promoted Friedel-Crafts acylation reactions.

Organic & biomolecular chemistry (2013-02-08)
Zhiliang Huang, Liqun Jin, Heyou Han, Aiwen Lei
ABSTRACT

AlCl(3) promoted Friedel-Crafts acylation between 4-tert-butylbenzoyl chloride and mesitylene was investigated. The donor-acceptor complex was observed as the major species. Kinetic investigation demonstrated that the reaction was first-order on the donor-acceptor complex and zero-order on ArH, suggesting that the donor-acceptor complex was not the true reactive species. However, the acylium ion was almost invisible with a fairly low concentration under live reaction conditions. It was approved as the true reactive species through kinetic data ("kinetic capture") in the AlCl(3) promoted Friedel-Crafts acylation reaction.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-tert-Butylbenzoyl chloride, 98%
Sigma-Aldrich
Aluminum chloride, anhydrous, sublimed, ≥98%
Sigma-Aldrich
Aluminum chloride solution, 1.0 M in nitrobenzene
Sigma-Aldrich
Aluminum chloride, reagent grade, 98%
Sigma-Aldrich
Aluminum chloride, ReagentPlus®, 99%