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- Title
Easy Access to Modified Cyclodextrins by an Intramolecular Radical Approach.
- Authors
Alvarez-Dorta, Dimitri; León, Elisa I.; Kennedy, Alan R.; Martín, Angeles; Pérez-Martín, Inés; Suárez, Ernesto
- Abstract
A simple method to modify the primary face of cyclodextrins (CDs) is described. The 6I- O-yl radical of α-, β-, and γ-CDs regioselectively abstracts the H5II, located in the adjacent D-glucose unit, by an intramolecular 1,8-hydrogen-atom-transfer reaction through a geometrically restricted nine-membered transition state to give a stable 1,3,5-trioxocane ring. The reaction has been extended to the 1,4-diols of α- and β-CD to give the corresponding bis(trioxocane)s. The C2-symmetric bis(trioxocane) corresponding to the α-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.
- Subjects
CYCLODEXTRINS; REGIOSELECTIVITY (Chemistry); TRANSITION state theory (Chemistry); X-ray diffraction; HOST-guest chemistry
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 12, p3745
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201412300