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Synthesis of Aniline Derivatives with Potential Toxicological Implications to the Spanish Toxic Oil Syndrome
Author(s) -
Ferrer Marta,
Galceran Montserrat,
SánchezBaeza Francisco,
Casas Josefina,
Messeguer Angel
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930184
Subject(s) - chemistry , aniline , residue (chemistry) , acylation , organic chemistry , regioselectivity , glycerol , yield (engineering) , polyunsaturated fatty acid , double bond , fatty acid , materials science , metallurgy , catalysis
The synthesis of anilides 2 from several saturated and unsaturated fatty acids 1 required for toxicological studies related to the Spanish Toxic Oil Syndrome is reported. In addition, a simple procedure for the microscale determination of the position of a carbon–carbon double bond of a fatty acid residue is described. This procedure involves epoxidation of the sample with 3,3‐dimethyldioxirane followed by oxidative cleavage with periodic acid to yield the corresponding carbonyl derivatives which are easily identifiable by GC‐MS analysis. Finally, the synthesis of anilino derivatives 5 – 8 formally derived from glycerol is also reported. For this purpose, a common precursor, i.e. 3‐(phenylamino)propane‐1,2‐diol ( 4 ) is prepared, and convenient procedures for its chemoselective acylation at either the hydroxy or the amino group have been developed.