Is the tert-butyl group bulky enough to end-cap a pseudorotaxane with a 24-crown-8-ether wheel?

Org Lett

Department of Organic and Polymeric Materials, Tokyo Institute of Technology, Ookayama, Meguro, Tokyo 152-8552, Japan.

Published: November 2004

Although rotaxane chemists have long believed that the tert-butyl group is bulkier than the cavity of dibenzo-24-crown-8-ether (DB24C8), it is essentially smaller than the cavity of DB24C8. The tert-butyl (or 4-tert-butylphenyl) group can actually function as an end-cap of DB24C8-based rotaxanes when the intercomponent interaction is effectively operative. When such attractive interaction is removed, deslippage occurs. [structure: see text]

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Source
http://dx.doi.org/10.1021/ol048135nDOI Listing

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