Polymer-mediated reactions. A Nazarov-like cyclization

Christopher Pavlik, Martha D. Morton, Michael A. Invernale, Ian D. Berghorn, Gregory A. Sotzing, Michael B. Smith

Research output: Contribution to journalArticle

Abstract

The polymer PEDOT+ mediates a Nazarov-like cyclization of dienones, in an heterogeneous system and in hydrocarbon solvents. The polymer-mediated reactions show clear differences in product formation when compared to the same reaction with tosic acid, or when compared to reports in the literature. Comparable or improved yields are observed, as well as the ability to give a -Nazarov product in cases where treatment with acid fails to give cyclization, or leads to an undesirable rearrangement. In addition, the ability to recycle the polymer makes this a potentially useful protocol for an important organic chemical reaction.

Original languageEnglish (US)
Article numberS04411ST
Pages (from-to)2195-2199
Number of pages5
JournalSynlett
Issue number15
DOIs
StatePublished - 2011

Keywords

  • -cyclopentenones
  • Nazarov cyclization
  • PEDOT
  • dienones
  • polymer

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Polymer-mediated reactions. A Nazarov-like cyclization'. Together they form a unique fingerprint.

  • Cite this

    Pavlik, C., Morton, M. D., Invernale, M. A., Berghorn, I. D., Sotzing, G. A., & Smith, M. B. (2011). Polymer-mediated reactions. A Nazarov-like cyclization. Synlett, (15), 2195-2199. [S04411ST]. https://doi.org/10.1055/s-0030-1261194