Non‐Ionic Template Synthesis of Amide‐Linked Rotaxanes: Olefinic and Aliphatic Axle Building Blocks

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The first synthesis of amide‐linked rotaxanes with non‐arene axle building blocks is reported. The threading synthesis of rotaxane 8 with olefinic fumaryl chloride proves that arene moieties are not necessary for non‐ionic template syntheses. Mass spectroscopic evidence of a rotaxane bearing an aliphatic axle, derived from succinic acid, revealed that hydrogen bonding, rather than π,π interactions, is the predominant template binding force. 1 H‐NMR titration studies on the threading synthesis of these mechanically bonded molecules were carried out. The association constants measured suggest that the incorporation of the corresponding monoamide monochloride (cf. 7 ), rather than the incorporation of the diacid dichloride (cf. 5 ), plays the key role in these rotaxane syntheses. The X‐ray structural analysis of a semi axle ( 14 ) reveals hydrogen bonding patterns characteristic of diamides.