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 |
|---|---|
| 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
Fingerprint Dive into the research topics of 'Easy access to modified cyclodextrins by an intramolecular radical approach'. Together they form a unique fingerprint.
Profiles
Equipment
Cite this
Alvarez-Dorta, D., León, E. I., Kennedy, A. R., Martin, A., Pérez-Martín, I., & Suárez, E. (2015). Easy access to modified cyclodextrins by an intramolecular radical approach. Angewandte Chemie International Edition, 54(12), 3674-3678. https://doi.org/10.1002/anie.201412300