Chemical modification of poly (methyl acrylate) via metalation and α - substitution

Jean M.J. Frechet*, Jean M. Farrall, C. Grant Willson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


Poly(methyl acrylate) was transformed into polymers containing α-substituted units by a two-step reaction sequence involving formation of a poly(enolate) by base abstraction of the hydrogens located α to the ester carbonyl groups, followed by reaction of the poly(enolate) with electrophiles such as carbon dioxide, sulfur dioxide, or ethyl bromoacetate. Further modification of the α-carboxylate or α-sulfinate polymers led to poly(acrylates) bearing α-methyl carboxylate, α-methyl sulfone, or α-(2-hydroxyethyl sulfone) functional groups. Quenching of the poly(enolate) with ethyl bromoacetate gave a polymer containing itaconate as well as acrylate units. In general, the degree of functionalization achieved was from 0.3 to 0.65.

Original languageEnglish (US)
Pages (from-to)567-573
Number of pages7
JournalPolymer Bulletin
Issue number11-12
StatePublished - Jul 1982
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry
  • Condensed Matter Physics
  • Polymers and Plastics
  • Materials Chemistry


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