A facile route to old and new cyclophanes via self-assembly and capture

Mary S. Collins, Matthew E. Carnes, Bryan P. Nell, Lev N. Zakharov and Darren W. Johnson ()
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Mary S. Collins: University of Oregon
Matthew E. Carnes: University of Oregon
Bryan P. Nell: University of Oregon
Lev N. Zakharov: Center for Advanced Materials Characterization in Oregon (CAMCOR), 1241 University of Oregon
Darren W. Johnson: University of Oregon

Nature Communications, 2016, vol. 7, issue 1, 1-7

Abstract: Abstract Cyclophanes are a venerable class of macrocyclic and/or cage compounds that often feature high strain, unusual conformations and quite surprising properties, many of which are legendary in physical organic chemistry. However, the discovery of new, diverse cyclophanes and derivatives has been hindered by syntheses that are traditionally low-yielding, requiring long reaction times, laborious purification steps and often extreme conditions. Herein, we demonstrate a new self-assembly route to a variety of discrete cyclic and caged disulfide structures, which can then be kinetically captured upon sulfur extrusion at room temperature to give a diversity of new thioether (hetera)cyclophanes in high yield. In addition to the synthesis of novel macrocycles (dimers through hexamers), this process provides an improved route to a known macrobicyclic trithiacyclophane. This technique also enables the facile isolation of a tetrahedral macrotricyclic tetrathiacyclophane in two steps at an ambient temperature.

Date: 2016
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DOI: 10.1038/ncomms11052

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