74526-84-4Relevant academic research and scientific papers
Intramolecular Benzyne–Phenolate [4+2] Cycloadditions
Hirano, Keiichi,Nishii, Arata,Ohmori, Ken,Suzuki, Keisuke,Takiguchi, Hiromu,Takikawa, Hiroshi,Tanaka, Masato,Uchiyama, Masanobu,Yagishita, Hirotoshi
supporting information, p. 12440 - 12444 (2020/05/25)
An intramolecular benzyne–phenolate [4+2] cycloaddition is reported. Benzyne precursors, having vicinal halogen-sulfonate functionalities, linked with a phenol(ate) by various tether groups undergo efficient intramolecular [4+2] cycloaddition by treatment with either Ph3MgLi or nBuLi for halogen–metal exchange to form various benzobarrelenes.
Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
Chatterjee, Anamitra,K?nig, Burkhard
supporting information, p. 14289 - 14294 (2019/08/30)
The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.
Synthesis and Demethylation of New 5,6,7,8-Tetrahydro-4,9-dimethoxy-1H-benzindole
Malesani, Giorgio,Ferlin, Maria Grazia,Masiero, Sergio
, p. 633 - 637 (2007/10/02)
The title compound 17 was prepared in good yield starting from 5,6,7,8-tetrahydro-1-naphthol (9) by an advantageous synthesis route consisting of eight steps, as indicated in Scheme 2.Demethylation by reflux heating with anhydrous aluminium chloride in dry benzene furnished 4,9-dihydroxy- and 4,9-dioxo-5,6,7,8-tetrahydro-1H-benzindoles (compounds 18 an 19, respectively).All new products were identified on the basis of spectral and analytical data.
