Easy access to modified cyclodextrins by an intramolecular radical approach

Dimitri Alvarez-Dorta, Elisa I. León, Alan R. Kennedy, Angeles Martin, Inés Pérez-Martín, Ernesto Suárez

Research output: Contribution to journalArticle

20 Citations (Scopus)
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Abstract

A simple method to modify the primary face of cyclodextrins (CDs) is described. The 6I-O-yl radical of a-, b-, and g-CDs regioselectively abstracts the H5II, located in the adjacent d-glucose unit, by an intramolecular 1,8-hydrogenatom-transfer reaction through a geometrically restricted ninemembered transition state to give a stable 1,3,5-trioxocane ring. The reaction has been extended to the 1,4-diols of a- and b-CD to give the corresponding bis(trioxocane)s. The C2-symmetric bis(trioxocane) corresponding to the a-CD is a stable crystalline solid whose structure was confirmed by X-ray diffraction analysis. The calculated geometric parameters confirm that the primary face is severely distorted toward a narrower elliptical shape for this rim.
Original languageEnglish
Pages (from-to)3674-3678
Number of pages5
JournalAngewandte Chemie International Edition
Volume54
Issue number12
Early online date28 Jan 2015
DOIs
Publication statusPublished - Mar 2015

Keywords

  • cyclodextrins
  • host-guest systems
  • hydrogen transfer
  • radical reactions
  • structure elucidation
  • reaction kinetics
  • x ray diffraction analysis

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