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Flexible, Long‐Chain Alkanediamines as Building Blocks for Catenanes – Steric Hindrance of Circumrotation by Derivatization
Author(s) -
Baumann Sven,
Jäger Ralf,
Ahuis Friedrich,
Kray Bernd,
Vögtle Fritz
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970420
Subject(s) - catenane , chemistry , steric effects , amide , derivatization , sulfonamide , combinatorial chemistry , stereochemistry , organic chemistry , molecule , high performance liquid chromatography
New catenanes of the amide‐linked type, such as 11 with one macrocycle containing two (CH 2 ) 12 chains are synthesized from long‐chain alkanediamines in yields of up to 21%. Consequently, the preorganization afforded by fixed and angular building units – so far considered essential – proves not to be necessary. The new sulfonamide catenanes exhibit high conformational flexibility. However, the circumrotation of one of the macrocycles can be hindered by substitution with bipyridine units at the sulfonamide nitrogen.