Terminal azide- (5) and alkyne-calixarenes (6) are accessible by the deprotonation of p-tert-butyltetramethoxycalix[4]arene (1) followed by regioselective nucleophilic substitution and elaboration of the attached group.  Compounds 5 and 6 undergo the Cu(I)-catalyzed 1,3-dipolar cycloaddition with the appropriate partner, providing 1,2,3-triazoles (7, 8, 9) attached to a calixarene via a linker at the methylene bridge. Compounds 3�9 have been characterized by multinuclear NMR spectroscopy and high-resolution mass spectrometry.

Click reaction of terminal azide- and alkyne-tethered <i>p-tert-</i>butylcalix[4]arenes

239th National Meeting (2010)

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Click reaction of terminal azide- and alkyne-tethered p-tert-butylcalix[4]arenes