The Experts below are selected from a list of 132 Experts worldwide ranked by ideXlab platform
N. S. Zefirov - One of the best experts on this subject based on the ideXlab platform.
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a simple nitration of electrophilic alkenes with Tetranitromethane in the presence of triethylamine synthesis of functionalized β nitroalkenes
Tetrahedron Letters, 2011Co-Authors: Yulia A Volkova, Elena B Averina, T S Kuznetsova, Yuri K Grishin, V B Rybakov, N. S. ZefirovAbstract:A convenient method for the preparation of functionalized β-nitroalkenes based on the nitration of α,α-di- and α,α,β-trisubstituted unsaturated aldehydes, ketones and esters with Tetranitromethane in the presence of triethylamine is described. Series of substituted β-nitroalcohols and β-nitroalkenes are obtained in good yields under mild conditions.
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ring opening of aziridines with Tetranitromethane in the presence of triethylamine efficient synthesis of β tosylamino nitrates
Tetrahedron Letters, 2010Co-Authors: Yuliya A Volkova, Elena B Averina, T S Kuznetsova, N. S. ZefirovAbstract:Abstract A convenient method for the preparation of β-tosylamino nitrates based on the ring-opening reaction of aziridines by Tetranitromethane in the presence of triethylamine is described. A series of substituted β-amino nitrates is obtained in high yields under mild conditions.
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Tetranitromethane as an efficient reagent for the conversion of epoxides into β hydroxy nitrates
Tetrahedron Letters, 2008Co-Authors: Yuliya A Volkova, Elena B Averina, Olga A Ivanova, T S Kuznetsova, Ekaterina M Budynina, N. S. ZefirovAbstract:A convenient regioselective method for the preparation of β-hydroxy nitrates based on the ring opening reaction of epoxides by Tetranitromethane in the presence of triethylamine is described. A series of substituted β-hydroxy nitrates were obtained in high yields under mild conditions.
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Specificity of the Reaction of Tetranitromethane with Alkenes in Nitromethane
Russian Journal of Organic Chemistry, 2005Co-Authors: O. A. Ivanova, T S Kuznetsova, E. B. Averina, E. M. Budynina, A. A. Korlyukov, M. Yu. Antipin, N. S. ZefirovAbstract:Reactions of Tetranitromethane with a number of di- and trisubstituted olefins in nitromethane were studied. Vinylcyclopropanes and phenylcycloalkenes reacted with Tetranitromethane in an unexpected fashion, leading to formation of alkyltrinitromethanes and vicinal nitro alcohols.
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Three-component Reactions of Tetranitromethane with Olefins
Russian Journal of Organic Chemistry, 2004Co-Authors: E. B. Averina, Yu K Grishin, T S Kuznetsova, O. A. Ivanova, E. M. Budynina, S. M. Gerdov, N. S. ZefirovAbstract:Three-component reactions of Tetranitromethane with two different olefins taken in equimolar amounts are procedures fit for preparation of 3,3-dinitroisoxalidines of a mixed composition.
Lennart Eberson - One of the best experts on this subject based on the ideXlab platform.
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the formation and reactions of adducts from the photochemical reactions of aromatic compounds with Tetranitromethane and other x no2 reagents invited review
Australian Journal of Chemistry, 1998Co-Authors: Lennart Eberson, M P HartshornAbstract:The formation and reactions are reviewed (see Contents below) of adducts from the photochemical reactions of aromatic compounds with Tetranitromethane and other X-NO2 reagents.
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Photochemical Nitration by Tetranitromethane. XXXII. Adduct Formation in the Photochemical Reaction of Phenanthrene and Tetranitromethane
Australian Journal of Chemistry, 1996Co-Authors: Craig P Butts, Lennart Eberson, M P Hartshorn, Karen L. Fulton, Ward T RobinsonAbstract:Photolysis of the phenanthrene/Tetranitromethane charge-transfer complex yields the triad of phenanthrene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad in dichloromethane at 20° gives 9-nitrophenanthrene (1), trans-10-trinitromethyl-9,10-dihydrophenanthren-9-yl nitrate (2a), trans-9-nitro-10-trinitromethyl-9,10-dihydrophenanthrene (2b), and trans-10-trinitromethyl-9,10-dihydrophenanthren-9-ol (2c). Adduct formation is partially suppressed when trifluoroacetic acid (0.7 M) is added to the dichloromethane solvent at 20°, the major product identified being 9-nitrophenanthrene (1). At -20° in dichloromethane, or in acetonitrile at 20°, 10'-nitro-9,9',10,10'-tetrahydro-9,9'-biphenanthren-10-yl nitrate (3) is formed, apparently by reaction of nitrogen dioxide with phenanthrene. X-Ray crystal structure determinations are reported for adducts (2a,b).
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keynote article photochemical nitration by Tetranitromethane part xix the competitive reactions of trinitromethanide and nitrogen dioxide with radical cations and their use for selective nitrations
Journal of The Chemical Society-perkin Transactions 1, 1994Co-Authors: Lennart Eberson, M P Hartshorn, Finn Radner, Jan Olof SvenssonAbstract:The photolysis of the charge-transfer complex between an aromatic compound (ArH) and Tetranitromethane is known to form initially a triad of the aromatic radical cation, trinitromethanide ion and NO2[eqn. (i)]. For reactive and moderately reactive radical cations, the chemical follow-up [graphic omitted] reactions from the species of the triad are fast at –60 °C, as shown by the fact that the solutions are EPR-silent during photolysis. However, by conducting the photolysis in the presence of a protic acid, the trinitromethanide ion is rendered unreactive by protonation, resulting in the build-up of a detectable (EPR) concentration of ArH˙+ or (ArH)2˙+. This shows that the initial chemical step from the triad is the nucleophilic attack of trinitromethanide ion upon ArH˙+, and that the rate of the reaction between the latter and NO2 must be significantly lower. Preparative experiments support this conclusion, in that the predominant adduct formation from ArH–Tetranitromethane photolysis is diverted into nitro substitution in the presence of a protic acid, the latter reaction occurring via ArH˙+–NO2 coupling.These findings also establish that results obtained from the photonitration of aromatics by Tetranitromethane are not relevant for judging the possible electron transfer nature of electrophilic aromatic nitration by nitronium ion.
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photochemical nitration by Tetranitromethane xiv the formation of 1 3 dipolar nitro addition products from the photochemical reaction of 1 2 dimethylnaphthalene and Tetranitromethane
Australian Journal of Chemistry, 1994Co-Authors: Craig P Butts, Lennart Eberson, J L Calvert, M P Hartshorn, N Maclaga, Ward T RobinsonAbstract:Photolysis of the 1,2-dimethylnaphthalene/Tetranitromethane charge-transfer complex yields the triad of 1,2-dimethylnaphthalene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad gives predominantly the adducts (13)-(16), each of which is formed by attack of the trinitromethanide ion at C4 of the 1,2-dimethylnaphthalene radical cation. Thermal cycloaddition in adducts (13) and (16) gives the cycloadducts (12) and (17) respectively.
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formation of a 1 3 dipolar nitro addition product from the photochemical reaction of 1 2 dimethylnaphthalene and Tetranitromethane
Journal of The Chemical Society Chemical Communications, 1993Co-Authors: Craig P Butts, Lennart Eberson, J L Calvert, M P Hartshorn, Ward T RobinsonAbstract:The photochemical reaction between Tetranitromethane and 1,2-dimethylnaphthalene gives, among other adducts, a product of internal 1,3-dipolar cycloaddition of a nitro group from the trinitromethyl group across the 1,2-double bond of the primary adduct, 1,2-dimethyl-r-3-nitro-4-trinitrometnyl-3,4-dihydronaphthalene.
F. Radner - One of the best experts on this subject based on the ideXlab platform.
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LIGHT-INITIATED AND THERMAL NITRATION REACTIONS DURING PHOTOLYSIS OF NAPHTHALENE/Tetranitromethane OR 1-METHOXYNAPHTHALENE/Tetranitromethane IN DICHLO ROMETHANE
Journal of the American Chemical Society, 1991Co-Authors: L. Eberson, F. RadnerAbstract:The photolysis of naphtalene or 1-methoxynaphthalene together with Tetranitromethane in dichloromethane, using light with a cuttof at λ
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light initiated and thermal nitration reactions during photolysis of naphthalene Tetranitromethane or 1 methoxynaphthalene Tetranitromethane in dichlo romethane
Journal of the American Chemical Society, 1991Co-Authors: L. Eberson, F. RadnerAbstract:The photolysis of naphtalene or 1-methoxynaphthalene together with Tetranitromethane in dichloromethane, using light with a cuttof at λ<435 nm, has been investigated. It is shown that naphthalene, a representative of less reactive aromatics, predominantly (85-90%) reacts to give nitro compounds with a low α/β ratio (ca. 1.5) via a photochemical addition/elimination mechanism, the remaining part being formed via thermal, NO 2 -promoted nitration (α/β ratio ca. 20). The adducts are formed by photochemical excitation of the CT complex between naphthalene and Tetranitromethane, resulting in formation of the triad [ArH .+ NO 2 (NO 2 ) 3 C − ] from which the observed chemistry develops by attack of trinitromethanide upon the radical cation. For 1-methoxynaphthalene, a representative of more highly reactive aromatics, the reaction is again photochemically initiated and again adducts seem to be responsible for the further development of thermal nitration reactions, apart from the NO 2 -induced reaction
Ward T Robinson - One of the best experts on this subject based on the ideXlab platform.
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Photochemical Nitration by Tetranitromethane. XXXII. Adduct Formation in the Photochemical Reaction of Phenanthrene and Tetranitromethane
Australian Journal of Chemistry, 1996Co-Authors: Craig P Butts, Lennart Eberson, M P Hartshorn, Karen L. Fulton, Ward T RobinsonAbstract:Photolysis of the phenanthrene/Tetranitromethane charge-transfer complex yields the triad of phenanthrene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad in dichloromethane at 20° gives 9-nitrophenanthrene (1), trans-10-trinitromethyl-9,10-dihydrophenanthren-9-yl nitrate (2a), trans-9-nitro-10-trinitromethyl-9,10-dihydrophenanthrene (2b), and trans-10-trinitromethyl-9,10-dihydrophenanthren-9-ol (2c). Adduct formation is partially suppressed when trifluoroacetic acid (0.7 M) is added to the dichloromethane solvent at 20°, the major product identified being 9-nitrophenanthrene (1). At -20° in dichloromethane, or in acetonitrile at 20°, 10'-nitro-9,9',10,10'-tetrahydro-9,9'-biphenanthren-10-yl nitrate (3) is formed, apparently by reaction of nitrogen dioxide with phenanthrene. X-Ray crystal structure determinations are reported for adducts (2a,b).
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photochemical nitration by Tetranitromethane xiv the formation of 1 3 dipolar nitro addition products from the photochemical reaction of 1 2 dimethylnaphthalene and Tetranitromethane
Australian Journal of Chemistry, 1994Co-Authors: Craig P Butts, Lennart Eberson, J L Calvert, M P Hartshorn, N Maclaga, Ward T RobinsonAbstract:Photolysis of the 1,2-dimethylnaphthalene/Tetranitromethane charge-transfer complex yields the triad of 1,2-dimethylnaphthalene radical cation, nitrogen dioxide, and trinitromethanide ion. Recombination of this triad gives predominantly the adducts (13)-(16), each of which is formed by attack of the trinitromethanide ion at C4 of the 1,2-dimethylnaphthalene radical cation. Thermal cycloaddition in adducts (13) and (16) gives the cycloadducts (12) and (17) respectively.
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formation of a 1 3 dipolar nitro addition product from the photochemical reaction of 1 2 dimethylnaphthalene and Tetranitromethane
Journal of The Chemical Society Chemical Communications, 1993Co-Authors: Craig P Butts, Lennart Eberson, J L Calvert, M P Hartshorn, Ward T RobinsonAbstract:The photochemical reaction between Tetranitromethane and 1,2-dimethylnaphthalene gives, among other adducts, a product of internal 1,3-dipolar cycloaddition of a nitro group from the trinitromethyl group across the 1,2-double bond of the primary adduct, 1,2-dimethyl-r-3-nitro-4-trinitrometnyl-3,4-dihydronaphthalene.
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The addition–elimination mechanism in the photonitration of naphthalene by Tetranitromethane
Journal of The Chemical Society Chemical Communications, 1992Co-Authors: Lennart Eberson, M P Hartshorn, Finn Radner, Ward T RobinsonAbstract:By the isolation and kinetic studies of an adduct (cis-1,4-dihydro-1-nitro-4-trinitromethylnaphthalene) from the photolysis of naphthalene–Tetranitromethane in dichloromethane or acetonitrile, it is shown that the route to nitro substitution products proceeds via addition–elimination, the latter step being either thermal or base-catalysed.
L. Eberson - One of the best experts on this subject based on the ideXlab platform.
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LIGHT-INITIATED AND THERMAL NITRATION REACTIONS DURING PHOTOLYSIS OF NAPHTHALENE/Tetranitromethane OR 1-METHOXYNAPHTHALENE/Tetranitromethane IN DICHLO ROMETHANE
Journal of the American Chemical Society, 1991Co-Authors: L. Eberson, F. RadnerAbstract:The photolysis of naphtalene or 1-methoxynaphthalene together with Tetranitromethane in dichloromethane, using light with a cuttof at λ
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light initiated and thermal nitration reactions during photolysis of naphthalene Tetranitromethane or 1 methoxynaphthalene Tetranitromethane in dichlo romethane
Journal of the American Chemical Society, 1991Co-Authors: L. Eberson, F. RadnerAbstract:The photolysis of naphtalene or 1-methoxynaphthalene together with Tetranitromethane in dichloromethane, using light with a cuttof at λ<435 nm, has been investigated. It is shown that naphthalene, a representative of less reactive aromatics, predominantly (85-90%) reacts to give nitro compounds with a low α/β ratio (ca. 1.5) via a photochemical addition/elimination mechanism, the remaining part being formed via thermal, NO 2 -promoted nitration (α/β ratio ca. 20). The adducts are formed by photochemical excitation of the CT complex between naphthalene and Tetranitromethane, resulting in formation of the triad [ArH .+ NO 2 (NO 2 ) 3 C − ] from which the observed chemistry develops by attack of trinitromethanide upon the radical cation. For 1-methoxynaphthalene, a representative of more highly reactive aromatics, the reaction is again photochemically initiated and again adducts seem to be responsible for the further development of thermal nitration reactions, apart from the NO 2 -induced reaction
