NEW AND CONVENIENT SYNTHESIS OF 3-METHYLENEPENT-4-ENOIC ACID BY ELECTROCHEMICAL CARBOXYLATION

Authors
TOKUDA M YOSHIKAWA A SUGINOME H SENBOKU H
Citation
M. Tokuda et al., NEW AND CONVENIENT SYNTHESIS OF 3-METHYLENEPENT-4-ENOIC ACID BY ELECTROCHEMICAL CARBOXYLATION, Synthesis, (10), 1997, pp. 1143
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
10
Year of publication
1997
Database
ISI
SICI code
0039-7881(1997):10<1143:NACSO3>2.0.ZU;2-F
Abstract
Electrochemical carboxylation of 2-bromomethyl-1,4-dibromobut-2-ene (1 ) with atmospheric carbon dioxide in a DMF solution containing Bu4NI w ith a platinum cathode and a manganin or nickel anode gave 3-methylene pent-4-enoic acid (3) in 57 % yield. The acid 3 can be used as a diene in an aqueous intermolecular Diels-Alder reaction with dimethyl fumar ate to give the adduct 7 in 67 % yield.