Friedel-Crafts acylation with cyclic anhydrides

Friedel-Crafts acylation can be carried out with cyclic anhydrides, in which case the product contains a carboxyl group in the side chain. When succinic... 

Friedel-Crafts acylation can be carried out with cyclic anhydrides,272 in which case the product contains a carboxyl group in the side chain. When succinic anhydride is used, the product is ArCOCH2CH2COOH. This can be reduced (9-37) to A1CH2CH2CFLCOOH, which can then be cyclized by an internal Friedel-Crafts acylation. The total process is called the Haworth reaction 173... 

Succinic anhydride, the structure of which is shown, is a cyclic anhydride often used in Friedel-Crafts acylations. Give the structure of the product obtained when benzene is acylated with succinic anhydride in the presence of aluminum chloride. 

I. Hashimoto, T. Kawaji, F. D. Badea, T. Sawada, S. Mataka, M. Tashiro, G. Fukata, Regioselectivity of Friedel-Crafts Acylation of Aromatic-Compounds with Several Cyclic Anhydrides, Res. Chem. Intermed. 1996, 22, 855-869. 

There is one way to avoid umpolung and that is to make the disconnection outside the 1,4 relationship. As it happens, we have already seen this strategy in action (p, 799), It involves a Friedel-Crafts acylation of benzene (Chapter 22) with a cyclic anhydride and leads directly to this... 

The alkylaluminum halide-induced Friedel-Crafts acylation is a very general and synthetically useful reaction that allows the functionalization of unsaturated fatty compounds. Acylations were carried out with different acylating agents such as acyl chlorides, dicarboxylic acid dichlorides, cyclic anhydrides, unsaturated acyl chlorides, and aromatic and heteroaromatic carboxylic acid chlorides, yielding a large... 

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