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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

✍ Scribed by Quermann, Rolf ;Maletz, Reinhard ;Schäfer, Hans J.

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 507 KB
Volume: 1993
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.1993199301197

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✦ Synopsis

Abstract

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.

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