The addition of nitrile oxides to C60

Mark S. Meier, Magdalena Poplawska

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

The 1,3-dipolar cycloaddition of nitrile oxides to C60 is described. These reactions result in the formation of fullerene-fused isoxazoline heterocycles bearing a series of different substituents in 3-position. The preparation and spectroscopic characterization of these compounds are reported, as well as some investigations of the reactivity of these heterocycles. It is found that fullerene isoxazolines are less reactive than aliphatic isoxazolines.

Original languageEnglish
Pages (from-to)5043-5052
Number of pages10
JournalTetrahedron
Volume52
Issue number14
DOIs
StatePublished - Apr 1 1996

Bibliographical note

Funding Information:
ACKNOWLEDGMENTS The authors wish to thank the University of Kentucky Special Equipment Fund for the purchase of the electrochemical equipment used in this study. We thank Dr. Thomas Guarr (Gentex Corp, Zeeland, MI) for assistance in performing the electrochemical measurements. We also thank Professor Jan Pyrek of the University of Kentucky College of Pharmacy, and Professor Vahid Majidi and Mr. Robert Pogue of the Department of Chemistry for assistance with mass spectra. The authors also thank the Vice Chancellor for Research and Graduate Studies of the University of Kentucky for a Postdoctoral Fellowship for M. P.. This research was supported by the National Science Foundation (Grant CHE-9404704) and by Kentucky EPSCoR program (NSF Grant EHR-91-08764 and DE-FG02-91ER75657) The authors also thank the National Science Foundation (CHE-9113581) for equipment.

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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