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

Abstract

The synthesis of twelve alkylthio- or perfluoroalkylpropanethio-α-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 α-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.