Cyclic fatty acid monomers: synthesis and characterization of methyl ω-(2-alkylcyclopentyl) alkenoates and alkanoates

Add time:08/23/2019    Source:sciencedirect.com

Some 1,2-disubstituted cyclopentanes were synthesized. These were methyl 9-(2-butyl-cyclopentyl)-8-nonenoate, methyl 7-(2-hexyl-cyclopentyl)-6-heptenoate and methyl 5-(2-octyl-cyclopentyl)-4-pentenoate and their corresponding alkanoates. The synthesis involved a Michaël addition of alkylmagnesium bromide to an unsaturated cyclic ester. The resulting cis and trans ethyl 2-alkylcyclopentane carboxylate were further converted to the alcohols then to the aldehydes. The aldehydes were condensed with the ylide derived from the (ω-carboxyalkyl)-triphenylphosphonium bromide and methylsulfinylmethide in DMSO to give unsaturated C18 cyclic fatty acid monomers. These cyclic fatty acids were further converted to the methyl esters and the ethylenic bond was reduced by 1H-nuclear magnetic resonance (NMR), mass spectrometry coupled with GLC (GC-MS) and infra-red spectroscopy (IR).

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