Lock, J.May, B.Clements, P.Tsanaktsidis, J.Easton, C.Lincoln, S.2007-02-252007-02-252001Organic and Biomolecular Chemistry, 2001; 1(24):3361-33641477-05200300-922Xhttp://hdl.handle.net/2440/4700© Royal Society of Chemistry 2001Acylation of the primary amine group of 6^A-(6-aminohexylamino)-6^A-deoxy-α-cyclodextrin 1 by 4-nitrophenyl trinorbornane-2-acetate 6, 1-methoxycarbonyl-8-(4-nitrophenoxycarbonyl)cubane 7, 1-methoxycarbonyl-2,3-dimethyl-8-(4-nitrophenoxycarbonyl)cubane 8, and 1-(4-nitrophenoxycarbonyl)adamantane 9, respectively, gives 6^A-deoxy-[6-(trinorbornan-2-ylacetylamino)hexylamino]-α- cyclodextrin 2, 6^A-[6-(8-carboxycuban-1-ylcarbonyl-amino)hexylamino]-6 ^A-deoxy-α-cyclodextrin 3, 6^A-[6-(8-carboxy-2,3-dimethylcuban-l-ylcarbonylamino)hexylamino]- 6^A-deoxy-α-cyclodextrin 4, and 6^A-[6-(adamantan-1-ylcarbonylamino)hexylamino]-6^A- deoxy-α-cyclodextrin 5, in good yields together with 4-nitrophenolate. In basic D²O, the substituents of 1-4 complex intramolecularly within the α-cyclodextrin annulus, whereas that of 5 does not due to its larger size, as shown by ¹H ROESY NMR spectroscopy. This facilitates a mechanistic comparison with the formation of βCD analogues of 2-5.enJournal article002001200310.1039/b107324a0001726594000192-s2.0-003554397561127