Fatty acids Friedel Crafts acylation

Friedel-Crafts acylation of unsaturated fatty acids can be carried out with succinic anhydride ia the presence of alkyl aluminium haUde (104). 

The antiasthamtic activity of the sulfur-free substituted long chain fatty acid seratrodast (59-5) is attributed to the antagonism of thromboxanes, whose structures also include a fatty side chain, rather than to leukotrienes. Friedel-Crafts acylation of benzene with the acid chloride from monomethyl pimelate (59-1) leads to... 

Unsaturated fatty compounds are of interest as renewable raw materials (1). These compounds can be functionalized at the C,C-double bond by electrophilic addition reactions to give new oleochemicals with potentially new and interesting properties. The alkylaluminum chloride-induced Friedel-Crafts acylation of unsaturated fatty compounds (Fig. 1), such as oleic acid [la], 10-undecenoic acid [2a], petroselinic acid [3a], and erucic acid [4a], and the respective esters and alcohols yield the corresponding P,y-unsaturated ketones (2,3). 

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... 

Metzger, J.O., and U. Biermann, Lewis Acid Induced Addition to Unsaturated Fatty Com-poimds rV Synthesis of Cyclopentenones from Friedel-Crafts Acylation Products of Unsaturated Fatty Compounds with a,P-Unsaturated Chlorides, Fett/Lipid 100 2-6 (1998). 

Although the general scope of direct acylation of olefins under Friedel-Crafts conditions is rather limited, it has been demonstrated that such reactions can be applied to glycals like 162 to produce C-2 acylated glycals 163 in excellent yields and selectivity (O Scheme 54). Moreover, as reagents, the long-chain fatty acid based acylating species have been shown to be as effective as acetyl chloride [255]. 

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