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Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C C ipso-substitution reaction using proton-exchanged montmorillonite as media

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Abstract We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density… Click to show full abstract

Abstract We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density functional theory calculations support a plausible mechanism, which includes a distinctive aromatic C C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.

Keywords: exchanged montmorillonite; transformation hydroxy; unusual transformation; methoxybenzylic alcohols; hydroxy methoxybenzylic; proton exchanged

Journal Title: Tetrahedron Letters
Year Published: 2020

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