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Conversion of Fatty Acids and Derivatives, IV. Conversion of Fatty Acid Methyl Esters into Dialkylated Succinic Esters by Oxidative Coupling of their Enolates
Author(s) -
Quermann Rolf,
Maletz Reinhard,
Schäfer Hans J.
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301197
Subject(s) - chemistry , succinic acid , oxidative phosphorylation , oxidative coupling of methane , dimer , fatty acid , coupling (piping) , organic chemistry , bromide , succinates , catalysis , biochemistry , mechanical engineering , engineering
The enolates of fatty acid methyl esters 1a – g are dimerized in good yields (56 to 73%) by means of oxidative coupling with copper(II) bromide to dialkylated succinic esters 2a – g . The configuration of meso ‐ 2a was established by independent synthesis. On treatment with ozone the unsaturated dimer 2c is converted to the tetracarboxyl compound 6 . Epoxidation of 2g leads to the corresponding bisepoxy diester 7 .