Synthesis 2018; 50(19): 3897-3901
DOI: 10.1055/s-0037-1609574
paper
© Georg Thieme Verlag Stuttgart · New York

An Expedient Synthesis of Ketocalix[6]arene Hexamethyl Ether

Norbert Itzhak
Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem 9190401, Israel   Email: silvio.biali@mail.huji.ac.il
,
Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem 9190401, Israel   Email: silvio.biali@mail.huji.ac.il
› Author Affiliations
This work was supported by Israel Science Foundation (ISF) (Grant No. 223/14).
Further Information

Publication History

Received: 28 May 2018

Accepted after revision: 12 June 2018

Publication Date:
05 July 2018 (online)


Abstract

p-tert-Butylcalix[6]arene hexamethyl ether was oxidized in one step to the corresponding ketocalix[6]arene via photochemical bromination (100 W spot lamp) with NBS in a chloroform/water mixture. A pentamethyl ketocalix[6]arene derivative was obtained by reaction of the ketocalix[6]arene hexamethyl ether with boron tribromide dimethyl sulfide complex, and characterized by X-ray crystallography. In the presence of base, the compound undergoes an intramolecular nucleophilic aromatic substitution reaction.

Supporting Information

 
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