Synthesis of Aryl-substituted 2-methoxyphenol Derivatives from Maltol-derived Oxidopyrylium Cycloadducts Through an Acid-mediated Ring Contraction Cascade

Overview

Journal Chem Commun (Camb)

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2020 Feb 19

PMID 32068199

Citations 2

Authors

Lauren P Bejcek

Ryan P Murelli

Affiliations

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Abstract

Oxidopyrylium cycloadducts derived from maltol and aryl acetylenes undergo acid-mediated rearrangements to generate aryl-substituted 2-methoxyphenol (guaiacol) derivatives. Specifically, the cycloadducts react with boron trichloride to form 2-methoxy-5-arylphenol molecules, and with methane sulfonate to form 2-methoxy-4-aryl-6-methylphenol molecules.

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