SYNTHESIS OF ANILINE DERIVATIVES WITH POTENTIAL TOXICOLOGICAL IMPLICATIONS TO THE SPANISH TOXIC OIL SYNDROME

The synthesis of anilides 2 from several saturated and unsaturated fat ty acids 1 required for toxicological studies related to the Spanish T oxic Oil Syndrome is reported. In addition, a simple procedure for the microscale determination of the position of a carbon-carbon double bo nd of a fatty acid residue is described. This procedure involves epoxi dation of the sample with 3,3-dimethyldioxirane followed by oxidative cleavage with periodic acid to yield the corresponding carbonyl deriva tives which are easily identifiable by GC-MS analysis. Finally, the sy nthesis of anilino derivatives 5 - 8 formally derived from glycerol is also reported. For this purpose, a common precursor, i.e. 3-(phenylam ino)propane-1,2-diol (4) is prepared, and convenient procedures for it s chemoselective acylation at either the hydroxy or the amino group ha ve been developed.