New Journal of Chemistry, 2007, 31, 1899 - 1906

Synthesis and characterisation of O-6-alkylthio- and perfluoroalkylpropanethio--cyclodextrins and their O-2-, O-3-methylated analogues

Bernard Bertino Ghera, Florent Perret, Anne Baudouin, Anthony W. Coleman and Hélène Parrot-Lopez

The synthesis of twelve alkylthio- or perfluoroalkylpropanethio--cyclodextrin derivatives and their O-2-, O-3-methylated analogues are described. The coupling reaction involves firstly the basic in situ hydrolysis of alkylperfluoropropane isothiouronium iodide or alkylisothiouronium bromide, then reaction with an -cyclodextrin modified at the C-6 position by an iodine or methylsulfonyl group. The interfacial properties of these new compounds have been determined by the studies of their mono-molecular layer at the air–water interface.