Revisiting the 'Phenonium Phenomenon': Regiodivergent Opening of Nonsymmetrical Phenonium Ions with Halide Nucleophiles

Hannah M. Holst, Shelby B. McGuire, Nicholas J. Race

Research output: Contribution to journalArticlepeer-review

Abstract

Formation of phenonium ions through anchimeric assistance (neighboring-group participation) of aryl rings has been known since 1949. Although these reactive intermediates have been studied extensively by physical organic chemists, their potential as control elements in synthesis is underutilized. Presented here are our laboratory's recently reported first examples of regiodivergent openings of nonsymmetrical phenonium ions with chloride nucleophiles. The selectivity of these processes is under reagent control. The reactions are operationally simple and permit the stereospecific synthesis of complex chiral building blocks from readily accessible epoxide starting materials. 1 Introduction 2 Select Examples of Phenonium Ion Methodology 3 Regiodivergent Opening of Nonsymmetrical Phenonium Ions 4 Summary and Outlook.

Original languageEnglish (US)
Pages (from-to)1-6
Number of pages6
JournalSynlett
Volume32
Issue number1
DOIs
StatePublished - Jan 5 2021

Bibliographical note

Funding Information:
This work was funded by the University of Minnesota and the American Chemical Society Petroleum Research Fund (PRF 60782-DNI1).AmeicanChemical SocietyPetoleumReseachFundPRF60782-DNI1)UniverityofMinneota()

Keywords

  • epoxides
  • halides
  • neighboring-group effects
  • rearrangement
  • regioselectivity
  • stereoselective synthesis

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