Browsing by Author "Snayer, Tregen M."

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    Facile synthesis of a C4-symmetrical inherently chiral calix[4]arene†
    (Royal Society of Chemistry, 2021-09) Hodson, Luke; Visagie, Kevin J.; Smith, Michael-Phillip; Loots, Leigh; Kuter, David; Snayer, Tregen M.
    Inherently chiral calix[4]arenes with C4-symmetry are extremely rare and difficult to synthesise, severely hampering any effort to expand on their potential as chiral supramolecular catalysts and building blocks. Herein we report a reaction of a tetracarbamate calix[4]arene with NBS which results in a high yield of an inherently chiral calix[4]arenes with C4-symmetry. Furthermore, employing a chiral N-Boc proline moiety allows for separation of the diastereomers formed, thus obtaining the pure enantiomers after hydrolysis. The enantiomers could be assigned based on the CD spectra and DFT calculated values.
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    ipso-Bromination of tert-butylcalix[4]arenes
    (ARKAT USA, 2020) Snayer, Tregen M.; Bose, Sritama; Arnott, Gareth E.
    The ipso-bromination of calix[4]arenes using bromine has been investigated and provides a direct method to tetra-bromocalix[4]arene in a single step in excellent yield (>90%). The method is also applicable to directly forming tribromocalix[4]arene in appreciable amounts (>60%). It was found during this study that a number of important reaction variables were very important for success, namely exclusion of light, temperature control, purity of starting material, solvent used and rate of bromine addition.