32465-70-6Relevant articles and documents
Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media
Chen, Dongyin,Chen, Xuan,Dong, Zezhong,Jiang, Nan,Li, Fei,Yun, Yangfang,Zhou, Yu
supporting information, (2020/11/12)
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[sbnd]C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.
Attempted Synthesis of a Stable, Quintet, Tetraphenoxyl Tetraradical: Facile Rearrangement of a Substituted Bicyclobutane
Anderson, Kraig K.,Shultz, David A.,Dougherty, Dennis A.
, p. 7575 - 7584 (2007/10/03)
The preparation of tetraphenol 3 and its attempted oxidation to tetraradical 2 are described. Tetraphenoxyl 2 was envisioned as a more stable analog of the previously reported, quintet tetraradical 1. However, EPR studies on 3 and model compounds and crystallographic characterization of the product from oxidation of 3 suggest that 2 is not a viable target. Apparently, 2 or an intermediate in the multistep oxidation path leading to it undergoes a ring closure to a bicyclobutane. The bicyclobutane, in turn, undergoes a surprisingly facile rearrangement to the analogous butadiene structure.