Issue 85, 2018
From the journal:

Chemical Communications

Selective monoalkylation of p-tert-butylcalix-[4]-arene in a methyl carbonate ionic liquid†

R. E. Whiteside, ORCID logo *a   H. Q. Nimal Gunaratne, ORCID logo a   A. F. V. Muzioa  and  P. Nockemann ORCID logo *a  

* Corresponding authors

a QUILL Research Centre, School of Chemistry and Chemical Engineering, Queen's University of Belfast, Stranmillis Road, Belfast, Northern Ireland BT9 5AG, UK
E-mail: rwhiteside05@qub.ac.uk, p.nockemann@qub.ac.uk

Abstract

Methyl carbonate ionic liquids are shown to readily mono-deprotonate p-tert-butylcalix-[4]-arenes initiating the formation of an organic mono-anionic p-tert-butylcalix-[4]-arate salt, methanol and carbon dioxide. These calix-[4]-arate salts have been successfully used in alkylation reactions with dialkyl sulfates and alkyl halides to form a mono-alkylated single product with high yield. This method avoids the common use of alkali metal bases such as caesium fluoride hence providing a safer and more selective synthetic route.

Graphical abstract: Selective monoalkylation of p-tert-butylcalix-[4]-arene in a methyl carbonate ionic liquid

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Article information

DOI
https://doi.org/10.1039/C8CC05566A
Article type
Communication
Submitted
10 Jul 2018
Accepted
28 Sep 2018
First published
01 Oct 2018

Chem. Commun., 2018,54, 12037-12040

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Selective monoalkylation of p-tert-butylcalix-[4]-arene in a methyl carbonate ionic liquid

R. E. Whiteside, H. Q. N. Gunaratne, A. F. V. Muzio and P. Nockemann, Chem. Commun., 2018, 54, 12037 DOI: 10.1039/C8CC05566A

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