Mechanochemical Solvent‐Free Conditions for the Synthesis of Pillar[5]arene‐Containing [2]Rotaxanes. Issue 21 (1st March 2019)

• Record Type: Journal Article
• Authors: Holler, Michel; Stoerkler, Timothée; Louis, Alexandra; Fischer, Fanny; Nierengarten, Jean‐François
• Other Names: Sauvage Jean‐Pierre guestEditor.
• Is Part Of: European journal of organic chemistry. Issue 21(2019)
• Page Start: 3401
• Page End: 3405
• Publication Date: 2019-03-01
• Subjects: Ball‐mill -- Mechanochemistry -- Pillar[5]arene -- Rotaxanes -- Supramolecular chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900153
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Pillar[5]arene‐containing [2]rotaxanes have been efficiently prepared under solvent‐free conditions. Specifically, solid‐to‐solid ball‐milling of primary or secondary amine reagents with the inclusion complex resulting from the association of dodecanedioyl dichloride and a pillar[5]arene derivative provided the corresponding diamide [2]rotaxanes in good to excellent yields. Importantly, [2]rotaxanes difficult or even impossible to prepare under classical reaction conditions in solution, are now easily obtained. Abstract : Solid‐to‐solid ball‐milling of amine reagents and the inclusion complex resulting from the association of dodecanedioyl dichloride and a pillar[5]arene derivative provided the corresponding diamide [2]rotaxanes in good to excellent yields.