Authors Hanashima, M; Matsumura, T; Asaji, Y; Yoshimura, T; Matsuo, J in PHARMACEUTICAL SOC JAPAN published article about TANDEM WESSELY OXIDATION; CYCLOADDITION; ALKALOIDS; ADDITIONS in [Hanashima, Mika; Matsumura, Toshiki; Asaji, Yuta; Yoshimura, Tomoyuki; Matsuo, Jun-ichi] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan in 2020.0, Cited 40.0. Computed Properties of C13H8O2. The Name is 6H-Benzo[c]chromen-6-one. Through research, I have a further understanding and discovery of 2005-10-9
Regioselectivity for intramolecular Diels-Alder (IMDA) reactions of 6-acetoxy-6-alkenylcyclohexa-2,4-dien-1-ones that were formed by oxidation of 2-alkenylphenols with lead tetraacetate in acetic acid were studied. Bridged regioselectivity was observed in the IMDA reactions of 6-acetoxy-6-alkenylcyclohexa-2,4-dien-1-ones having a dienophile part which could conjugate with an aromatic group. Bridged seven-and eight-membered rings and bicyclo[2.2.2]octane skeletons were constructed by the present IMDA reactions. Density functional theory (DFT) calculations suggested that conjugation of the dienophile with neighboring aromatic groups lowered the highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) energy gap and preceded bridged [4 + 2] adducts.
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Reference:
Article; Zhang, Jian; Shi, Dongdong; Zhang, Haifeng; Xu, Zheng; Bao, Hanyang; Jin, Hongwei; Liu, Yunkui; Tetrahedron; vol. 73; 2; (2017); p. 154 – 163;,
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