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

15 Citations (Scopus)

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.
LanguageEnglish
Pages3674-3678
Number of pages5
JournalAngewandte Chemie International Edition
Volume54
Issue number12
Early online date28 Jan 2015
DOIs
Publication statusPublished - Mar 2015

Fingerprint

Cyclodextrins
X-Ray Diffraction
X ray diffraction analysis
Glucose
Crystalline materials

Keywords

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

Cite this

Alvarez-Dorta, Dimitri ; León, Elisa I. ; Kennedy, Alan R. ; Martin, Angeles ; Pérez-Martín, Inés ; Suárez, Ernesto. / Easy access to modified cyclodextrins by an intramolecular radical approach. In: Angewandte Chemie International Edition. 2015 ; Vol. 54, No. 12. pp. 3674-3678.
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Alvarez-Dorta, D, León, EI, Kennedy, AR, Martin, A, Pérez-Martín, I & Suárez, E 2015, 'Easy access to modified cyclodextrins by an intramolecular radical approach' Angewandte Chemie International Edition, vol. 54, no. 12, pp. 3674-3678. https://doi.org/10.1002/anie.201412300

Easy access to modified cyclodextrins by an intramolecular radical approach. / Alvarez-Dorta, Dimitri; León, Elisa I.; Kennedy, Alan R.; Martin, Angeles; Pérez-Martín, Inés; Suárez, Ernesto.

In: Angewandte Chemie International Edition, Vol. 54, No. 12, 03.2015, p. 3674-3678.

Research output: Contribution to journalArticle

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AU - Suárez, Ernesto

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KW - structure elucidation

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