1820-59-3Relevant academic research and scientific papers
Method for nitrating aromatic compound by using nitrate under the action of auxiliary agent
-
Paragraph 0067; 0068, (2018/09/11)
The invention discloses a method for nitrating an aromatic compound by using a nitrate under the action of an auxiliary agent, and provides an aromatic nitro compound preparation method, which comprises: in the presence of an external action and an auxiliary agent, carrying out a nitrating reaction on an aromatic compound and a metal nitrate or a hydrate thereof to obtain the aromatic nitro compound, wherein the external action can cause the physical and/or chemical property change of a substance, the auxiliary agent is a substance having water absorbing ability, the external action can be mechanical force or heating, and the mechanical force can be any one selected from compression, shearing, impacting, friction, stretching, bending and vibration. According to the present invention, the method does not require any solvents so as to avoid the generation of the waste liquid; the acidic substance is not used, such that the treatment is simple after the reaction is completed, and the equipment is not damaged; the added auxiliary agent can be theoretically recycled; and the method has extremely high conversion rate and extremely high selectivity, and can be used for the nitration of conventional aromatic compounds.
Approaches to prepare perfluoroalkyl and pentafluorophenyl copper couples for cross-coupling reactions with organohalogen compounds
Kremlev, Mikhail M.,Mushta, Aleksej I.,Tyrra, Wieland,Yagupolskii, Yurii L.,Naumann, Dieter,Sch?fer, Mathias
, p. 19693 - 19699 (2015/11/27)
The reactions of iodoperfluoroalkanes CnF2n+1I (n = 2, 3, 4) and n-BuLi at low temperatures give NMR spectroscopic evidence for LiCnF2n+1 which were converted into LiCu(CnF2n+1)2 derivatives upon treatment with 0.5 mol copper(i) bromide, CuBr. An alternative route to obtain perfluoroorgano copper couples, Cu(Rf)2Ag (Rf = n-C3F7, n-C4F9, C6F5) was achieved from the reactions of the corresponding perfluoroorgano silver(i) reagents, AgRf, and elemental copper through redox transmetallations. The composition of the resulting reactive intermediates was investigated by means of 19F NMR spectroscopy and ESI mass spectrometry. Perfluoro-n-propyl and perfluoro-n-butyl copper-silver reagents prepared by the oxidative transmetallation route exhibited good properties in C-C bond formation reactions with acid chlorides even under moderate conditions. Substitution of bromine directly bound to aromatics for perfluoroalkyl groups was achieved at elevated temperatures, while success in halide substitution reactions using lithium copper couples remained poor.
Synthesis of indoles via palladium[0]-mediated ullmann cross-coupling of o-halonitroarenes with α-halo-enones or -enals
Banwell, Martin G.,Kelly, Brian D.,Kokas, Okanya J.,Lupton, David W.
, p. 2497 - 2500 (2007/10/03)
(Matrix presented) Palladium[0]-mediated Ullmann cross-coupling of o-halonitrobenzene (1) and various related nitroarenes with a range of α-halo-enones (e.g., 2) or -enals readily affords the expected α-arylenones, e.g., 3, or -enals, which are converted into the corresponding indoles, e.g., 4, on reaction with dihydrogen in the presence of Pd on C.
Synthesis of substituted dibenzophospholes. Part 9. Preparation of two water-soluble phosphinic-polyphosphonic acids
Cornforth, John
, p. 2889 - 2893 (2007/10/03)
Several improvements, including a generally applicable method for reduction of aromatic nitro compounds to amines, were made to the preparation from 2,2′,4,4′-tetranitrobiphenyl of the meso atropisomer 1 of a bis-phosphonomethylated 4,6-diaryldibenzophosphole 5-oxide, previously obtained in impure form.2 A concomitant product 12 containing one phosphonomethyl group was formed by a novel intramolecular displacement. Both products were converted by a specially developed method3 into crystalline phosphinic-polyphosphonic acids, containing respectively four and three phosphonomethyl groups, which formed stable monodisperse solutions in water at pH 2-4. These solutions catalysed the hydration of 2-methylpropene to fert-butyl alcohol somewhat more efficiently than a toluene-4-sulfonic acid solution of equivalent acidity.
SYNTHESIS OF 5-NITRO-5-(4-NITROPHENYL)-1,3-TETRAHYDROOXAZINES AND 5-NITRO-5-(1-ARYLOXYMETHYL)-1,3-TETRAHYDROOXAZINES, AND HEXAHYDROPYRIMIDINES IN NUCLEOPHILIC AROMATIC SUBSTITUTION
Galeeva, A. G.,Trifonova, V. N.,Kasatkina, A. A.,Zorin, V. V.,Rakhmankulov, D. L.
, p. 1019 - 1021 (2007/10/02)
The lithium salts of 3-alkyl-5-nitro-1,3-tetrahydrooxazines and the lithium alcoholates of 5-hydroxymethyl-3-methyl-5-nitro-1,3-tetrahydrooxazine and 5-hydroxymethyl-1,3-dimethyl-5-nitrohexahydropyrimidine enter into nucleophilic aromatic substituent with p-dinitrobenzene and 2,4-dinitrobromobenzene to form 3-alkyl-5-nitro-5-(4-nitrophenyl)-1,3-tetrahydrooxazines, 3-methyl-5-nitro-5-(4-nitrophenyloxymethyl)-1,3-tetrahydrooxazine, and 1,3-dimethyl-5-nitro-5-(aryloxymethyl)hexahydropyrimidines.
SYNTHESIS OF POLYNITRO-SUBSTITUTED 2-CARBOXYBIPHENYLS
Adrievskii, A. M.,Poplavskii, A. N.,Dyumaev, K. M.
, p. 1195 - 1198 (2007/10/02)
Methods were developed for the synthesis of polynitro-substituted 2-carboxybiphenyls.During the nitration of 2-carboxybiphenyl under rigorous conditions or during the heating of nitro-substituted 2-carboxybiphenyls in concentrated sulfuric acid or high-strength oleum decarboxylation and cyclization occur with the formation of nitro-substituted biphenyls and fluorenone.
Synthesis of Substituted Dibenzophospholes. Part 2. Syntheses of Intermediate Biphenyls and Quaterphenyls
Cornforth, John,Sierakowski, Andrew F.,Wallace Timothy W.
, p. 2299 - 2316 (2007/10/02)
A general procedure for synthesis of 4",6'-dialkoxy-2',2"-diamino-m-quaterphenyls has been established.Copper(I) t-butoxide is used to prepare 2,6-dinitrophenyls from 1,3-dinitrobenzene and aryl iodides.One of the nitro-groups is then exchanged for a methoxy-group by sodium methoxide in hexamethylohosphoramide; the resulting 2-methoxy-6-nitrobiphenyls are then iodinated in the 5-position.Ullmann coupling then gives the dinitroquaterphenyls which are reduced to the diamines.An alternative route from 2,2',4,4'-tetranitrobiphenyl was explored; arylation was easy but alkoxydenitration was indiscriminate.Some 71 new derivatives of biphenyl, terphenyl, and quterphenyl are reported.
