期刊
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY
卷 113, 期 1, 页码 72-82出版社
WILEY
DOI: 10.1002/ejlt.201000116
关键词
alkynic fatty acid; omega-arylation; cyclotrimerization; methoxycarbonylation; pyridine; 2-pyridone
Dehydrogenation of double to triple bonds by bromination/dehydrobromination and triple bond isomerization by the alkyne zipper reaction provide a short and facile access to internal and terminal alkynic fatty acids. Thereby methyl 10-undecynoate, methyl 9-octadecynoate, methyl 17-octadecynoate and derivatives have been prepared from the corresponding alkenic fatty acids. Their conversions are reported: The hydrogen in the terminal alkynic fatty compounds is substituted in a omega-carboxylation and a palladium(0)-catalysed omega-arylation. With carbon monoxide/methanol internal alpha,beta-unsaturated monoesters and terminal unsaturated diesters are obtained under mild conditions by palladium(II)-catalysis. Furthermore dimer fatty acids with a pyridine and a 2-pyridone core are prepared by cyclotrimerizations of alkynic fatty compounds with alkylnitriles and N-phenylisocyanate.
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