Freidel-Crafts acylation

Please note that while the Friedel-Crafts acylation reaction is presented in discussions of addition-elimination reaction mechanisms, this reaction is actually an electrophilic aromatic substitution reaction. The correct mechanisms for a Freidel-Crafts acylation was presented in the solution for Problem 6 (h) from Chapter 7. 

When H3PM012O40 was used to catalyze acylation reactions some of the acid dissolved and the reactions were partially promoted by the acid in solution. The H4SiW]204o and H3PW12O40 catalysts, however, did not dissolve under the reaction conditions and were, therefore, effective promoters for liquid phase Freidel-Crafts acylation reactions.Supported and bulk heteropoly acids have also been used to promote vapor phase Freidel-Crafts alkylations and esterifications.. ... 

The efficient conversion of a ketone to a fused cyclopentenone of the general type outlined in Scheme 5 has been demonstrated by Paquette and coworkers.The overall strategy is illustrated in Scheme 6 and begins with Freidel-Crafts acylation of the cyclic vinylsilane (8) to give the enone (9), which undergoes... 

Materials. Compounds 1-8 and 10 and synthetic starting materials were obtained from Aldrich and used without purification unless otherwise stated. Compounds 9 and 11 were synthesized using the methods of Schlenk (37) et al via the Freidel-Crafts acylation (38, 39). All other inhibitors were prepared by standard methods. Elemental analysis was provided by Atlantic Microlabs. 

Havinga et al. prepared a series of poly(o)-(pyrrol-3-yl)alkanesulfonates) for electrochemical study [7] (Figure 20.34). Their synthetic route involved protecting the A-position with benzenesulfonyl chloride to form the A-phenylsulfonyl derivative. The pyrrole was then acylated at the 3-position of pyrrole with a o>-haloacid chloride under Freidel-Crafts conditions, followed by a Clemmensen reduction to yield the... 

---