Issue 9, 2008
From the journal:

New Journal of Chemistry

Reactions of thiacalix[4]arene 1,3-bistriflate: formation of thiacalix[2]phenoxathiins—structural and complexation studies†

Almeqdad Habashneh,a   Chester R. Jablonski,a   Julie Collinsb  and  Paris E. Georghiou*a  

* Corresponding authors

a Department of Chemistry, Memorial University of Newfoundland, St. John’s, Newfoundland, NL, Canada
E-mail: parisg@mun.ca

b CREAIT, Memorial University of Newfoundland, St. John’s, Newfoundland, NL, Canada

Abstract

Reaction of the 1,3-bistriflate of thiacalix[4]arene 2 under various conditions including typical Sonogashira and other basic conditions with CuI, afforded a mixture of hydrolysis and rearrangement products including a bis(phenoxathiin) 3 reported also by Hattori and co-workers. An unprecedented displacement of a narrow-rim triflate by a hydrogen atom to form a new partial conethiacalixarene 2i is reported as are five new X-ray crystal structures. The de-tert-butylated analogue 3a was synthesized from 3 and their complexation properties with Ag+ and Hg2+ are also reported.

Graphical abstract: Reactions of thiacalix[4]arene 1,3-bistriflate: formation of thiacalix[2]phenoxathiins—structural and complexation studies

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Article information

DOI
https://doi.org/10.1039/B801483C
Article type
Paper
Submitted
28 Jan 2008
Accepted
16 May 2008
First published
09 Jun 2008

New J. Chem., 2008,32, 1590-1596

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Reactions of thiacalix[4]arene 1,3-bistriflate: formation of thiacalix[2]phenoxathiins—structural and complexation studies

A. Habashneh, C. R. Jablonski, J. Collins and P. E. Georghiou, New J. Chem., 2008, 32, 1590 DOI: 10.1039/B801483C

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