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 language | English |
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Pages (from-to) | 3674-3678 |
Number of pages | 5 |
Journal | Angewandte Chemie International Edition |
Volume | 54 |
Issue number | 12 |
Early online date | 28 Jan 2015 |
DOIs | |
Publication status | Published - Mar 2015 |
Keywords
- cyclodextrins
- host-guest systems
- hydrogen transfer
- radical reactions
- structure elucidation
- reaction kinetics
- x ray diffraction analysis