50885-07-9Relevant articles and documents
Total syntheses of cytotoxic, naturally occurring kalasinamide, geovanine, and marcanine A
Lang, Steffen,Groth, Ulrich
, p. 911 - 913 (2009)
(Chemical Equation Presented) Two novel synthetic strategies were developed for the natural products geovanine, marcanine A, and kalasinamide. The nine-step synthesis of geovanine marks its first total synthesis. The three compounds are known for their an
Direct nitration method of electron-enriched aromatic hydrocarbons
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Paragraph 0078-0080, (2018/10/02)
The invention discloses a direct nitration method of electron-enriched aromatic hydrocarbons, and belongs to the field of organic synthesis. The direct nitration method is a novel green free radical nitration method; aromatic hydrocarbons are taken as raw materials, acetonitrile, dichloromethane, chloroform, or acetone is taken as a reaction solvent, at room temperature conditions, the raw materials and green nitration reagent tert-butyl nitrite (TBN) are subjected to free radical nitration so as to obtain nitro-aromatic compounds. According to the direct nitration method, no metal is adoptedin reaction, tert-butyl nitrite is directly adopted in nitration reaction. Electron-donating groups such as OMe are introduced, the electron density of aromatic compounds is increased, the nitration reaction possibility is increased. The using amount of tert-butyl nitrite is reduced; only a product and tert-butyl alcohol are generated, environment pollution is reduced. The direct nitration methodis promising in application prospect in the field of nitro-aromatic compound synthesis, green nitration is realized, and a novel idea is provided for large-scale industrialized nitro-aromatic compoundproduction.
Photochemical nitration by tetranitromethane. Part XLI. Addition ipso to a methoxy group and the effect of methanol in the photochemical reaction between 1,4-dimethoxynaphthalene and tetranitromethane
Butts, Craig P.,Eberson, Lennart,Hartshorn, Michael P.,Persson, Ola,Thompson, Rewi S.,Robinson, Ward T.
, p. 1066 - 1077 (2007/10/03)
The photolysis of the charge transfer complex between 1,4-dimethoxynaphthalene and tetranitromethane in dichloromethane gives mainly 1,4-dimethoxy-2-nitronaphthalene (1), 1,4-dimethoxy-2-trinitromethylnaphthalene (2) and 4-methoxy-2-(dinitromethylene)-1(2H)-naphthalenone (3) together with smaller amounts of the labile adducts 1,4-dimethoxy-2-trinitromethyl-1,2-dihydronaphthalen-1-ol (4), 1,4-dimethoxy-2-nitro-1-trinitromethyl-1,2-dihydronaphthalene (5) and 1,4-dimethoxy-1-nitro-2-trinitromethyl-1,2-dihydronaphthalene (6). Photolysis in acetonitrile gives higher yields of adducts 4 and 5. Photolysis in dichloromethane containing methanol gives mainly 1,1,4-trimethoxy-2-trinitromethyl-1,2-dihydronaphthalene (7) and 1,1,4-trimethoxy-2-nitro-1,2-dihydronaphthalene (8). Photolysis in acetonitrile containing methanol gives high yields of 8 and 4,4-dimethoxy-3-nitro-3,4-dihydro-1(2H)-naphthalenone (9). The formation of adducts via attack of trinitromethanide ion or nitrogen dioxide ipso to a methoxy group during the photolysis of 1,4-dimethoxynaphthalene and tetranitromethane is discussed, and arguments are presented that such adducts give compounds 2 and 3 via rearrangement and/or elimination reactions. The effect of methanol and the mode of formation of compounds 7-9 via nucleophilic addition or nucleophilic displacement are discussed. X-Ray crystallographic structures are reported for 1,4-dimethoxy-2-trinitromethylnaphthalene (2) and 4-methoxy-2-(dinitromethylene)-1(2H)-naphthalenone (3). Acta Chemica Scandinavica 1997.
