CHIRAL AMIDE ROTAXANES WITH GLUCOSE STOPPERS - SYNTHESIS, CHIROPTICALPROPERTIES AND WHEEL-AXLE INTERACTIONS

In this paper we report on amide rotaxanes with tetrabenzoylglucose st oppers. When acetyl groups are used instead of benzoyl groups, merely a pseudo-rotaxane 5 is obtained. The circular dichroism measurements o f the rotaxanes 6a and 6b differ significantly from that one of the fr ee axle 7. Similarly, the Cotton effects of the mixtures of achiral wh eels 2a and 2b and chiral axle indicate intermolecular host-guest inte ractions, likewise. After an addition of a solution of NaOMe the wheel is slipping off immediately and quantitatively by hydrolysis, as the benzoylglucose stoppers decrease in size by hydrolysis.