26474-39-5Relevant academic research and scientific papers
New geometric isomers of oxooctadecadienoate in copper-catalyzed decomposition products of linoleate hydroperoxide
Tokita, Masako,Iwahara, Jyunko,Morita, Makio
, p. 993 - 997 (1999)
Methyl linoleate hydroperoxide produced by autoxidation was refluxed with 10-4 M Cu-naphthenate in benzene. Two new geometrical isomers of oxooctadecadienoate (compounds I and II) were found in addition to the four known isomers. They were isolated by a Sephadex LH-20 column chromatography with chloroform-hexane (2:1) and purified by HPLC on Nucleosil 100-5 and Zorbax ODS columns. UV, IR, MS, and 1H-NMR spectra were measured. The geometry of conjugated dienes were assigned from the coupling constants of the olefinic protons. Compounds I and II were identified as 13-oxo-trans-9, cis-11- and 9-oxo-cis-10, trans-12-octadecadienoate, respectively. Each of them had a cis double bond adjacent to the oxo group. The hydroperoxides of the same geometry as compounds I and II were also detected in autoxidation products.
Allylic oxidation: Easy synthesis of alkenones from activated alkenes with TEMPO
Breton, Tony,Liaigre, Denis,Belgsir, El Mustapha
, p. 2487 - 2490 (2007/10/03)
Activated alkenes and dienes are converted into the corresponding alkenone in excellent yields (>90%). In aqueous acetonitrile, the transformations are catalyzed by 2,2,6,6-tetramethyl-1-oxopiperidinium (TEMPO+) in the presence of water and 2,6-lutidine. TEMPO+ cations were regenerated electrochemically from the radical parent (TEMPO.) at a vitreous carbon anode.
