102898-11-3Relevant academic research and scientific papers
Oxocarbons and related compounds. 27. Synthesis of dihydrocyclobuta[a]naphthalene-1,2-diones and cyclobuta[a]naphthalene-1,2-diones via annulation of alkoxy-(1-alkenyl)benzenes with 3-chloro-3-cyclobutene-1,2-dione. Scope and limitations
Schmidt, Arthur H.,Kircher, Gunnar,Spring, Mathias,Hendriok, Markus W.,Kuenz, Christian
, p. 564 - 574 (2007/10/03)
The reaction of alkoxy-(1-alkenyl)benzenes with semisquaric chloride (3) has been investigated systematically. 1,2-Dialkoxy- and 1-alkoxy′-2-alkoxy″-4-(1-alkenyl)benzenes (6a-j) and (11a-i) react with 3 to give the 3,4-dihydrocyclobuta[a]naphthalene-1,2-diones(8a-j) and (12a-i). Treatment of the dihydrocyclobuta[a]naphthalene-1,2-diones with 1.2 equiv. bromine effects dehydrogenation and affords cyclobuta[a]naphthalene-1,2-diones(9a-e) and (13b-f). Any efforts to extend this annulation reaction to dimethoxy-(1-alkenyl)benzenes with the methoxy groups in other than the 1,2-positions, e. g. 14a, b, 16a, b have been unsuccessful. The reaction of 1,2,3-trimethoxy-4-(1-propenyl) [and 4-(1-butenyl)]-benzenes (18a) and (18b) with semisquaric chloride (3) leads to the elimination of HCl and CH3OH and gives 5,6-dimethoxy-3-methyl [and 3-ethyl]-cyclobuta[a]naphthalene-1,2-diones (20a) and (20b). The reaction pathway of this novel annulation reaction is discussed.
Studies on chromium trioxide-based oxidative coupling reagents and synthesis of lignan-cagayanone
Kuo,Lin
, p. 1507 - 1512 (2007/10/02)
Oxidation of 1-arylprop-1-enes by using the reagent system CrO3-HClO4- CH3CN at 0-5°C gave seven products from methyl isoeugenol, five from ethyl isoeugenol, four from benzyl isoeugenol, and five from isosafrole. Cagayanone was obtained from isosafrole in one step. The structures of the products were elucidated and the mechanism of their formation is discussed.
