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Zafrani Y, Cohen Y. Calix[4, 5]tetrolarenes: A New Family of Macrocycles. Org Lett. 2017;19(14):3719-3722doi: 10.1021/acs.orglett.7b01511.
Zafrani, Y., & Cohen, Y. (2017). Calix[4, 5]tetrolarenes: A New Family of Macrocycles. Organic letters, 19(14), 3719-3722. https://doi.org/10.1021/acs.orglett.7b01511
Zafrani, Yossi, and Cohen, Yoram. "Calix[4, 5]tetrolarenes: A New Family of Macrocycles." Organic letters vol. 19,14 (2017): 3719-3722. doi: https://doi.org/10.1021/acs.orglett.7b01511
Zafrani Y, Cohen Y. Calix[4, 5]tetrolarenes: A New Family of Macrocycles. Org Lett. 2017 Jul 21;19(14):3719-3722. doi: 10.1021/acs.orglett.7b01511. Epub 2017 Jun 29. PMID: 28661682.
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Org Lett. 2017 Jul 21;19(14):3719-3722. doi: 10.1021/acs.orglett.7b01511. Epub 2017 Jun 29.

Calix[4, 5]tetrolarenes: A New Family of Macrocycles.

Organic letters

Yossi Zafrani, Yoram Cohen

Affiliations

  1. School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University , Ramat Aviv 69978, Tel Aviv, Israel.
  2. The Department of Organic Chemistry, Israel Institute for Biological Research , Ness-Ziona 74000, Israel.

PMID: 28661682 DOI: 10.1021/acs.orglett.7b01511

Abstract

The facile and efficient one-step synthesis and the full characterization of novel π-electron rich macrocycles, calix-[n]tetrolarenes (n = 4, 5), are described. The tetramer and the much rarer sized pentamer were easily prepared by reaction of the commercially available, partially methylated 1,2,3,5-benzenetetrol with paraformaldehyde under TFA catalysis, with a total isolated yield of 73%. The reaction is solvent sensitive, and the number of methylated oxygens also affects the tetramer/pentamer distribution. The compounds formed may be considered as "chimeric" macrocycles of calixarene and pyrogallol[n]arene that may serve as new building blocks in host-guest and supramolecular chemistry.

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