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

Selective monoalkylation of p-tert-butylcalix-[4]-arene in a methyl carbonate ionic liquid.
Chem Commun (Camb). 2018 Oct 08;:
Authors: Whiteside RE, Gunaratne HQN, Muzio AFV, Nockemann P
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.
PMID: 30294733 [PubMed - as supplied by publisher]

Source: Chemical Communications - October 8, 2018 Category: Chemistry Authors: Whiteside RE, Gunaratne HQN, Muzio AFV, Nockemann P Tags: Chem Commun (Camb) Source Type: research