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Lewis‐acid catalysed ene reaction of electrondeficient aldehydes and ketones at unsaturated fatty acid derivatives
Author(s) -
Behr Arno,
Fiene Martin
Publication year - 2000
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/(sici)1438-9312(200003)102:3<212::aid-ejlt212>3.0.co;2-2
Subject(s) - chemistry , yield (engineering) , adduct , lewis acids and bases , ene reaction , glyoxylic acid , organic chemistry , oleic acid , stoichiometry , catalysis , medicinal chemistry , biochemistry , materials science , metallurgy
The SnCl 4 catalysed reaction of oleic acid ethyl ester (1) with glyoxylic acid ethyl ester (2) or mesoxalic acid diethyl ester (5) proceeds with good results yielding the corresponding 1:1‐adducts. Besides the ene adducts also δ‐lactones are formed by the reaction of (1) with (5) . The product yield shows a strong dependency on type and quantity of the Lewis‐acid used. A maximum yield was obtained with a stoichiometric amount of SnCl 4 . In contrast to the thermal ene reaction about 75% of the yield was attained already during the first 30 min of the reaction.