Unconventional Synthesis and Conformational Flexibility of Bis(1-triptycyl) Ether

Article abstract of DOI:10.1021/jo01300a069

The title compound was prepared by the thermolysis in perfluorodecalin of 1-triptycyl 1-triptyceneperoxycarboxylate which in turn was obtained by the reaction of 1-triptycyllithium with oxygen followed by treatment with 1-triptycenecarbonyl chloride.No sign of restricted rotation around the bridgehead-to-oxygen bonds of the ether was indicated by the 1H and 13C NMR spectra in spite of its overcrowded molecular framework.