Dimethyl disulfide derivatization of ethyl (9Z,12Z)-9, 12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate.
The dimethyl disulfide derivatization of ethyl (9Z,12Z)-9,12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate was studied. These methylene-interrupted dienes were reacted with dimethyl disulfide and I2 for 72 h at 50 degrees C and the tetrahydrothiopyran, thietane, and tetrahydrothiophene derivatives thus obtained were analyzed by gas chromatography-mass spectrometry. Each configurational isomer displayed a unique gas chromatography trace for the 4-, 5- and 6-membered ring cyclization products thus obtained. Therefore, the cis-cis and trans-trans double bond stereochemistry of 9,12-octadecadienoates can now be determined by dimethyl disulfide derivatization.
Carballeira
N M
NM
Department of Chemistry, University of Puerto Rico, San Juan 00931-3346. ncarball@upracd.upr.clu.edu
Cruz
C
C
D002849:Chromatography, Gas; D004220:Disulfides / Q000737:chemistry*; D004952:Esters; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure
D004220:Disulfides; D004952:Esters; D005231:Fatty Acids, Unsaturated; C027369:octadecadienoic acid; C021181:dimethyl disulfide