Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via CC ipso-substitution reaction using proton-exchanged montmorillonite as media. Issue 48 (26th November 2020)

• Record Type: Journal Article
• Authors: Chen, Xuan; Yun, Yangfang; Dong, Zezhong; Zhou, Yu; Li, Fei; Jiang, Nan; Chen, Dongyin
• Is Part Of: Tetrahedron letters. Volume 61:Issue 48(2020)
• Publication Date: 2020-11-26
• Subjects: Proton-exchanged montmorillonite -- Aromatic CC ipso-substitution -- Benzylic alcohol -- Diarylmethane -- Density functional theory; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152584
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: H-mont-mediated transformation of 4-hydroxy and 4-methoxybenzylic alcohols. An unusual type of aromatic CC ipso -substitution reaction. Nuclear magnetic resonance spectroscopy and density functional theory studies on the reaction mechanism. 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 CC ipso -substitution reaction with a hydroxymethyl group as the C-based leaving group.