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High‐Yielding Rotaxane Synthesis with an Anion Template
Author(s) -
Hübner Gosia M.,
Gläser Jens,
Seel Christian,
Vögtle Fritz
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990201)38:3<383::aid-anie383>3.0.co;2-h
Subject(s) - rotaxane , electrophile , nucleophile , chemistry , supramolecular chemistry , ether , hydrogen bond , stereochemistry , molecule , organic chemistry , catalysis
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.