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(2)rotaxanes as reagents for (3)rotaxane sythesis [i.e. synthesis]

WCU Author/Contributor (non-WCU co-authors, if there are any, appear on document)
Matthew Ben Hart (Creator)
Western Carolina University (WCU )
Web Site:
William Kwochka

Abstract: It was our hope to demonstrate that fairly simple systems such as a [2]rotaxane can itself be used as a reagent to synthesize even larger systems such a [3]rotaxane. This modular type approach offers several advantages over alternative methods. The [2]rotaxane was designed using a fumaramide template with a bulky diphenyl stopper on one end, and an aromatic core on the other end. The aromatic core contained three unique functional groups in the 1,3,5 position which allowed connection of the fumaramide thread, the tethering of the two [2]rotaxanes to form a single [3]rotaxane, and the removable stopper, tert-butyldiphenylsilyl ether. The aromatic core was synthesized from commercially available 5-Hydroxyisophathic acid using a novel and not fully understood selective reduction of only a single methyl ester of the 5-Hydroxyisophathic acid. Unfortunately, the repeated hydrolysis of the tert-butyldiphenylsilyl ether stopper prevented the completion of the full synthesis pathway, and the above mentioned modular approach was not able to be tested.

Additional Information

Language: English
Date: 2010
Rotaxanes -- Synthesis
Cyclic compounds -- Synthesis
Chemical tests and reagents