Abstract
Cyclopropanation of methyl esters of 10-undecenoic, oleic, elaidic, erucic,trans-2-docosenoic and a mixture of hydnocarpic and chaulmoogric acids was effected using diazomethane in the presence of palladium (II) acetate as catalyst. The products were isolated by silver ion thin-layer chromatography and characterized by infrared, proton nuclear magnetic resonance and mass spectrometric techniques. Terminally unsaturated, α, β-unsaturated and cyclopentene fatty acid esters were found to be more reactive than elaidate which in turn was more reactive than oleate. The reaction proceeds stereospecifically under milder conditions in a shorter time than with diiodomethane and zinc-copper couple.
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Gangadhar, A., Subbarao, R. & Lakshminarayana, G. Cyclopropanation of unsaturated fatty acid methyl esters using diazomethane and palladium (II) acetate. J Am Oil Chem Soc 65, 601–606 (1988). https://doi.org/10.1007/BF02540687
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DOI: https://doi.org/10.1007/BF02540687