Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade

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 sulfonat...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-03, Vol.56 (21), p.323-325
Main Authors: Bejcek, Lauren P, Murelli, Ryan P
Format: Article
Language:English
Subjects:
Aromatic compounds
Boron
Boron chlorides
Derivatives
Substitutes
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Summary: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. Maltol-derived oxidopyrylium cycloadducts undergo two different types of acid-mediated rearrangements to form 2-methoxyphenol derivatives.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09213g