High-Yielding Rotaxane Synthesis with an Anion Template

Gosia M Hübner; Jens Gläser; Christian Seel; Fritz Vögtle

doi:10.1002/(SICI)1521-3773(19990201)38:3<383::AID-ANIE383>3.0.CO;2-H

High-Yielding Rotaxane Synthesis with an Anion Template

Angew Chem Int Ed Engl. 1999 Feb 1;38(3):383-386. doi: 10.1002/(SICI)1521-3773(19990201)38:3<383::AID-ANIE383>3.0.CO;2-H.

Authors

Gosia M Hübner¹, Jens Gläser¹, Christian Seel¹, Fritz Vögtle¹

Affiliation

¹ Kekulé-Institut für Organische Chemie und Biochemie der Universität, Gerhard-Domagk-Strasse 1, D-53121 Bonn (Germany), Fax: (+49) 228-735662.

PMID: 29711647
DOI: 10.1002/(SICI)1521-3773(19990201)38:3<383::AID-ANIE383>3.0.CO;2-H

Abstract

An electrophile caught like a mouse in a trap! An anionic stopper-wheel complex acts as a supramolecular nucleophile in an almost quantitative synthesis of a phenyl ether rotaxane. The electrophilic semiaxle has to thread through the macrocycle in order to contact the bulky phenolate group that is positioned on the other side, and probably tightly held in place by hydrogen bonds.

Keywords: Host-guest chemistry; Nucleophilic substitutions; Rotaxanes; Supramolecular chemistry; Template synthesis.