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Cyclopropanation of unsaturated fatty acid methyl esters using diazomethane and palladium (II) acetate
Author(s) -
Gangadhar A.,
Subbarao R.,
Lakshminarayana G.
Publication year - 1988
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02540687
Subject(s) - diazomethane , cyclopropanation , elaidic acid , chemistry , organic chemistry , diiodomethane , palladium , catalysis , fatty acid , medicinal chemistry , linoleic acid , surface energy
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.