Transformation of a (4+6) Salicylbisimine Cage to Chemically Robust Amide Cages

Abstract: In recent years, interest in shape‐persistent organic cage compounds has steadily increased, not least because dynamic covalent bond formation enables such structures to be made in high to excellent yields. One often used type of dynamic bond formation is the generation of an imine bond from an aldehyde and an amine. Although the reversibility of the imine bond formation is advantageous for high yields, it is disadvantageous for the chemical stability of the compounds. Amide bonds are, in contrast to imine bonds much more robust. Shape‐persistent amide cages have so far been made by irreversible amide bond formations in multiple steps, very often accompanied by low yields. Here, we present an approach to shape‐persistent amide cages by exploiting a high‐yielding reversible cage formation in the first step, and a Pinnick oxidation as a key step to access the amide cages in just three steps. These chemically robust amide cages can be further transformed by bromination or nitration to allow post‐functionalization in high yields. The impact of the substituents on the gas sorption behavior was also investigated.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Transformation of a (4+6) Salicylbisimine Cage to Chemically Robust Amide Cages ; volume:131 ; number:26 ; year:2019 ; pages:8911-8915 ; extent:5 ; Angewandte Chemie ; 131, Heft 26 (2019), 8911-8915 (gesamt 5)

Contributors, Places and Time

• Creator: Bhat, Avinash S. ; Elbert, Sven M. ; Zhang, Wen‐Shan ; Rominger, Frank ; Dieckmann, Michael ; Schröder, Rasmus R. ; Mastalerz, Michael

Further information

• DOI: 10.1002/ange.201903631
• URN: urn:nbn:de:101:1-2022080808204149238130
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:33 AM CEST