Abstract
| 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 |
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Keywords
- cyclodextrins
- host-guest systems
- hydrogen transfer
- radical reactions
- structure elucidation
- reaction kinetics
- x ray diffraction analysis
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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 journal › Article
TY - JOUR
T1 - Easy access to modified cyclodextrins by an intramolecular radical approach
AU - Alvarez-Dorta, Dimitri
AU - León, Elisa I.
AU - Kennedy, Alan R.
AU - Martin, Angeles
AU - Pérez-Martín, Inés
AU - Suárez, Ernesto
PY - 2015/3
Y1 - 2015/3
N2 - 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.
AB - 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.
KW - cyclodextrins
KW - host-guest systems
KW - hydrogen transfer
KW - radical reactions
KW - structure elucidation
KW - reaction kinetics
KW - x ray diffraction analysis
UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773
U2 - 10.1002/anie.201412300
DO - 10.1002/anie.201412300
M3 - Article
VL - 54
SP - 3674
EP - 3678
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
IS - 12
ER -