Extracurricular laboratory: Synthetic route of C8H6O2

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Geiger, T; Haupt, A; Maichle-Mossmer, C; Schrenk, C; Schnepf, A; Bettinger, HF in [Geiger, Thomas; Haupt, Anne; Bettinger, Holger F.] Eberhard Karls Univ Tubingen, Inst Organ Chem, Morgenstelle 18, D-72076 Tubingen, Germany; [Maichle-Moessmer, Caecilia; Schrenk, Claudio; Schnepf, Andreas] Eberhard Karls Univ Tubingen, Inst Anorgan Chem, Morgenstelle 18, D-72076 Tubingen, Germany published Synthesis and Photodimerization of 2-and 2,3-Disubstituted Anthracenes: Influence of Steric Interactions and London Dispersion on Diastereoselectivity in 2019, Cited 84. Recommanded Product: 87-41-2. The Name is Isobenzofuran-1(3H)-one. Through research, I have a further understanding and discovery of 87-41-2.

There is increased evidence that the effect of bulky groups in organic, organometallic, and inorganic chemistry is not only repulsive but can be attractive because of London dispersion interactions. The influence of the size of primary alkyl substituents in 2- ‘ and 2,3-positions of anthracenes on the diastereoselectivity (anti vs syn dimer) of the [pi(4s) + pi(4s)] photoinduced dimerization is investigated. The synthesis of the anthracene derivatives was achieved by Suzuki-Miyaura reaction of 2,3-dibromoanthracene with alkylboronic acids as well as by reduction of anthraquinones that were obtained from 2,3-disubstituted 1,3-butadienes and naphthoquinone followed by dehydrogenation. The mixtures of dianthracene isomers were analyzed with respect to the anti/syn-ratio of the products by X-ray crystallography and nuclear Overhauser effect spectroscopy. While for the 2,3-dimethylanthracene the anti and syn isomers were formed in equal amounts, the anti dimers are the major products in all other cases. A linear correlation (R-2 = 0.98) between the steric size (Charton parameter) and the isomeric ratio suggests that the selectivity is dominated by classical repulsive steric effects. An exception is the iso-butyl substituent that produces an increased amount of the syn isomer. It is suggested that this is due to an exalted effect of London dispersion interactions.

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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem