Mechanical reconfiguration of stereoisomers

Kelly M. Wiggins, Todd W. Hudnall, Qilong Shen, Matthew J. Kryger, Jeffrey S. Moore, Christopher W. Bielawski

Research output: Contribution to journalArticle

Abstract

(Figure Presented) Poly(methyl acrylate) of varying molecular weight was grown from the enantiopure ditopic initiator (R)- or (S)-1,1′-binaphthyl- 2,2′-bis-(2-bromoisobutyrate). Subjecting CH3CN solutions of high-molecular-weight derivatives (MN > 25 kDa) to sonication at 0 °C resulted in >95% racemization after 24 h, as determined by circular dichroism; no appreciable racemization was observed in low-molecular-weight derivatives. Control experiments excluded the possibility of a thermal racemization mechanism.

Original languageEnglish (US)
Pages (from-to)3256-3257
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number10
DOIs
StatePublished - Mar 17 2010

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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