Dimethyl disulfide derivatization of ethyl (9Z,12Z)-9, 12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate

Chemistry and Physics of Lipids
N M Carballeira, C Cruz

Abstract

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.

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Citations

Aug 27, 2013·Insect Biochemistry and Molecular Biology·Takako AboshiNaoki Mori
Jun 7, 2011·Bioorganic & Medicinal Chemistry Letters·Muhammad Nadeem AkhtarNordin Hj Lajis

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