Propanoic acid, 3- Friedel-Crafts reaction

Intramolecular Friedel-Crafts acylation has been observed with bonellin dimethyl ester (20).53 The reaction proceeds in contrast to corresponding porphyrins, very smoothly with concentrated sulfuric acid because the propanoic acid side chain at the sp3 center is located above the macrocyclic ring system and therefore can better fulfill the stereoelectronic requirements for the ring-closure reaction. The ring closure is accompanied by racemization in the product 21. 

Pivaloylindole gives high yields of 6-substituted ketones on reaction with a-halo-acid-chlorides and aluminium chloride simple acid chlorides react only at 0-3. The sequence below shows how a 1-pivaloyl-3-(indol-3-yl)propanoic acid undergoes Friedel-Crafts cyclisation to C-4, away from the deactivated heterocyclic ring. °... 

One of the early examples of the use of sodium tetrachloroaluminate in intramolecular Friedel-Crafts acylation reactions involved the reaction shown in equation (49), in which P-(3-acenaphthoyl)propanoic acid was converted into perisuccinoylacenaphthene. The formation of the benzosuberanone ring system is particularly easy when electron-releasing substituents are present on the benzene ring. Under those cir-... 

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