A new approach to A,B-difunctionalisation of cyclodextrins using bulky 1,3-bis[bis(aryl)chloromethyl]benzenes as capping reagents.
1,3-Bis[bis(4-tert-butylphenyl)chloromethyl]benzene and 1,3-bis[bis(4-anisyl)chloromethyl]benzene were employed as regioselective capping reagents for the preparation of C-6A,C-6B-bridged, permethylated alpha- and beta-CD derivatives; isolated yields up to 55% of proximally capped, methylated CDs were obtained, thus opening the way to the straightforward preparation of a wide range of A,B-functionalised CDs. As revealed by a single crystal X-ray diffraction study, the benzene-1,3-bis[bis(4-tert-butylphenyl)methyl] spacer is perfectly suited for A,B-capping of beta-cyclodextrin.
Armspach
Dominique
D
Laboratoire de Chimie Inorganique Moléculaire, Université Louis Pasteur, UMR 7513 CNRS, 1 rue Blaise Pascal, 67008 Strasbourg cedex, France.
Poorters
Laurent
L
Matt
Dominique
D
Benmerad
Belkacem
B
Balegroune
Fadila
F
Toupet
Loic
L
D001555:Benzene Derivatives / Q000737:chemistry*; D003505:Cyclodextrins / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D001555:Benzene Derivatives; D003505:Cyclodextrins