Rofaxane Compoimnds, IThe name rotaxanes is suggested for newly synthesized aggregates of the type 1 consisting of a macrocycle and a chain with bulky end groups. As a model compound 4-(11-hydroxyundecy1)-catechol (11) can be ketalized with 1,21-dichlorheneicosan-l I-one to the benzodioxole 12. From the catechol-diol 16 the diansa compound 25b is synthesized which is then converted to the prerotaxane t6b with N-acety1-2,4,6-tri-p-tolylaniline, the structure of which is confirmed by the mass spectrum. T h e cleavage of the ketal 26b with hydrobromic acid affords the prerotaxane 27 coupled via N only, which after dehydrogenation and hydrolysis gives the rotaxane 29. Reductive acetylation leads to the hexaacetate 30. The corresponding non-rotaxane-like components, the pentaacetate 54 and the 1 -acetyl-I -aza-cyclohexacosan-14-one, are clearly different on thin layer chromatography from the rotaxane 30 which appears as a single spot with several mobile phases. The identical i.r.-spectrum of the rotaxane compounds 30 and of an equimolar mixture of the components (Fig. I ) confirms the postulated structure.

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Die 1,4‐Diaminobenzole (I) lassen sich mit langkettigen w‐Bromalkancarbonsäurechloriden (II) in 53 ‐ 83%iger Ausbeute zu den acylierten 1,4‐Diamin′obenzolen (III) umsetzen, deren Cyclisierung durch zweifache intramolekulare N‐Alkylierung mit NaH in Dimethylformamid nach dem Verdünnungsprinzip in 40‐54%iger Ausbeute die Diansa‐Verbindungen (IV) ergibt.