A one-step synthesis for cyclodextrin methacrylate monomers was examined starting from α-, β- and γ-cyclodextrin. The reaction of 2-isocyanatoethyl methacrylate as well as allylisocyanate with the corresponding cyclodextrin gave the monofunctionalized carbamate-linked cyclodextrin methacrylates2, 6and9and allylcarbamates11and14in moderate yields. By NMR spectroscopic means, it could be proven that in all cases only the primary 6-hydroxyl groups of the cyclodextrins reacted with the isocyanate group. For the synthesis of a β-cyclodextrin monoallyl compound, a substitution reaction of purchasable 6-O-monotoluenesulfonyl-β-cyclodextrin with allylamine gave 6-N-allylamino-6-deoxy-β-cyclodextrin18in high yield. The reaction of 2-isocyanatoethyl methacrylate with α-cyclodextrin to the 6-O-carbamoyl-2-methylpropenoylethyl-α-cyclodextrin(2)was optimized so that the monomer2could be prepared on a larger scale without chromatographic separation. The aqueous radical homopolymerization of2with the peroxodisulfate/bisulfite redox initiator gave the water soluble cyclodextrin polymer19in good yield. Its molecular weight was determined by gel permeation chromatography to beMn= 101,800 corresponding to an average degree of polymerizationPn= 90.