Chemistry with Roataxanes: Intra‐ and Intermolecularly Covalently Linked Rotaxanes

The direct introduction of sulfonamide units (cf. 9 ) into carboxamide‐based rotaxanes allows us to intramolecularly bridge the “wheel” and the “axle” of such species for the first time as is shown by the bridged bissulfonamide rotaxane 11 . Due to its stronger acidity the SO 2 ‐N H proton can be selectively abstracted by mild bases even in the presence of CO.N H and then be substituted by treatment with suitable iodo compounds. This leads intramolecularly to 11 (71% yield) and intermolecularly to bis[2]rotaxane 16 (76% yield). The iodo‐substituted rotaxane 15 isolated as a remarkably stable byproduct offers a new synthetic potential demonstrated by the preparation of 16 .