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. 2015 Mar 16;54(12):3674-8.
doi: 10.1002/anie.201412300. Epub 2015 Jan 28.

Easy access to modified cyclodextrins by an intramolecular radical approach

Dimitri Alvarez-Dorta  1 , Elisa I León, Alan R Kennedy, Angeles Martín, Inés Pérez-Martín, Ernesto Suárez
Affiliations
Free article

Easy access to modified cyclodextrins by an intramolecular radical approach

Dimitri Alvarez-Dorta et al. Angew Chem Int Ed Engl. .
Free article

Abstract

A simple method to modify the primary face of cyclodextrins (CDs) is described. The 6(I)-O-yl radical of α-, β-, and γ-CDs regioselectively abstracts the H5(II), 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.

Keywords: cyclodextrins; host-guest systems; hydrogen transfer; radical reactions; structure elucidation.

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