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Chiral Amide Rotaxanes with Glucose Stoppers – Synthesis, Chiroptical Properties and Wheel‐Axle Interactions
Author(s) -
Schmidt Thomas,
Schmieder Roland,
Müller Walter Manfred,
Kiupel Bernd,
Vögtle Fritz
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199809)1998:9<2003::aid-ejoc2003>3.0.co;2-u
Subject(s) - rotaxane , chemistry , amide , axle , hydrolysis , intermolecular force , slipping , circular dichroism , stereochemistry , supramolecular chemistry , organic chemistry , molecule , mechanical engineering , engineering
In this paper we report on amide rotaxanes with tetrabenzoylglucose stoppers. When acetyl groups are used instead of benzoyl groups, merely a pseudo‐rotaxane 5 is obtained. The circular dichroism measurements of the rotaxanes 6a and 6b differ significantly from that one of the free axle 7 . Similarly, the Cotton effects of the mixtures of achiral wheels 2a and 2b and chiral axle indicate intermolecular host‐guest interactions, 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.