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High‐Yield Synthesis of Ester, Carbonate, and Acetal Rotaxanes by Anion Template Assistance and their Hydrolytic Dethreading
Author(s) -
Reuter Carin,
Wienand Wolfgang,
Hübner Gosia M.,
Seel Christian,
Vögtle Fritz
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990903)5:9<2692::aid-chem2692>3.0.co;2-f
Subject(s) - rotaxane , supramolecular chemistry , acetal , nucleophile , yield (engineering) , carbonate , chemistry , hydrolysis , combinatorial chemistry , stereochemistry , organic chemistry , materials science , molecule , catalysis , metallurgy
The key intermediate in the synthesis of ester, carbonate and acetal rotaxanes is a new supramolecular anionic template, which consists of a “wheeled” phenolate that acts as a supramolecular nucleophile in a threading reaction, with up to 81 % yield. One result of this synthetic concept is the shown rotaxane that contains probably the shortest axle centre part ever incorporated in a rotaxane.