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Updated: Aug 27, 2026

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Published on: January 19, 2016
P(RNCH2CH2)3N: catalysts for the head-to-tail dimerization of methyl acrylate
Weiping Su1, Dale McLeod, John G Verkade
1Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Abstract:
The dimerization of methyl acrylate to the head-to-tail 2-methylene-pentanedioic acid dimethyl ester product was realized in 82 and 85% yield in only 4 h at room temperature in THF in the presence of catalytic amounts of P(RNCH2CH2)3N (R = i-Bu and Bn, respectively). These phosphines are to our knowledge the best nonmetallic catalysts so far reported for this reaction. In contrast, less sterically hindered P(MeNCH2CH2)3N failed to catalyze this dimerization, giving oligomer or polymer instead.
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