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Synthesis 2018; 50(03): 676-684
DOI: 10.1055/s-0036-1589127
DOI: 10.1055/s-0036-1589127
paper
Synthesis of Monofunctionalized Calix[5]arenes
Weitere Informationen
Publikationsverlauf
Received: 31. August 2017
Accepted after revision: 02. Oktober 2017
Publikationsdatum:
08. November 2017 (online)
Abstract
Seven OH-free and O-permethylated monofunctionalized calix[5]arenes carrying either additional methyl or tert-butyl groups are prepared following fragment condensation protocols. This strategy proves to be superior to previous approaches. Calix[5]arenes with free OH groups all adopt a cone conformation stabilized by a seam of hydrogen bonds at the lower rim. Post-condensation modifications, i.e., methylation of phenolic OH groups or functional group interconversions can also be achieved. Bulky tert-butyl groups are also found to stabilize the cone conformations of O-methylated compounds. These compounds offer versatile functional groups that make these concave molecules interesting building blocks for the synthesis of more sophisticated molecular architectures.
Key words
concave molecules - cyclophanes - calix[5]arenes - Duff reaction - fragment condensation strategySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589127.
- Supporting Information
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