- Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
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Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development. We recently described a series of oxalic acid diamides that are converted into active SCD inhibitors within a subset of cancers by CYP4F11-mediated metabolism. Herein, we describe the optimization of the oxalic acid diamides and related N-acyl ureas and an analysis of the structure-activity relationships related to metabolic activation and SCD inhibition.
- Winterton, Sarah E.,Capota, Emanuela,Wang, Xiaoyu,Chen, Hong,Mallipeddi, Prema L.,Williams, Noelle S.,Posner, Bruce A.,Nijhawan, Deepak,Ready, Joseph M.
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p. 5199 - 5221
(2018/06/13)
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- Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene
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The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.
- Akula, Pavan Sudheer,Hong, Bor-Cherng,Lee, Gene-Hsiang
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supporting information
p. 7835 - 7839
(2019/01/04)
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- INDOLE AHR INHIBITORS AND USES THEREOF
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The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.
- -
-
Paragraph 00657-00658
(2018/11/22)
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- Catalytic asymmetric Tamura cycloadditions involving nitroalkenes
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The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.
- Manoni, Francesco,Farid, Umar,Trujillo, Cristina,Connon, Stephen J.
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p. 1463 - 1474
(2017/02/15)
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- Enantioselective hydrogenation of α,β-disubstituted nitroalkenes
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The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.
- Li, Shengkun,Huang, Kexuan,Zhang, Xumu
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supporting information
p. 8878 - 8881
(2014/08/05)
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- One-pot solid phase synthesis of (E)-nitroalkenes
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An efficient one-pot protocol for the synthesis of (E)-nitroalkenes by reaction of aldehydes and nitroalkanes in the presence of polymer-bound triphenylphosphine, iodine and imidazole is described. Although the reaction works with similar efficiency with triphenylphosphine and its polymer-bound version, easy removal of the unwanted polymer-bound triphenylphosphine oxide and its recovery as triphenylphosphine provide the edge for practical application of the method.
- Rokhum, Lalthazuala,Bez, Ghanashyam
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p. 5500 - 5504
(2013/09/23)
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- Synthesis of nitroalkenes involving a cooperative catalytic action of iron(III) and piperidine: A one-pot synthetic strategy to 3-alkylindoles, 2H-chromenes and N-arylpyrrole
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An efficient and simple strategy has been developed to synthesize various substituted nitroalkenes involving a cooperative catalytic system of FeCl 3 and piperidine. This dual catalytic protocol simultaneously activates both electrophile and nucleophile and works under mild reaction conditions so that many sensitive functional groups were tolerated. Moreover, this cooperative catalytic reaction is also suitable for various one-pot reactions involving nitroalkenes such as, 2H-chromenes, N-arylpyrrole and Michael reaction with indole. Notably, this method is low-cost, efficient and environmentally friendly. Copyright
- Jalal, Swapnadeep,Sarkar, Soumen,Bera, Krishnendu,Maiti, Sukhendu,Jana, Umasish
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supporting information
p. 4823 - 4828
(2013/08/23)
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- Design of phosphorus ligands with deep chiral pockets: Practical Synthesis of chiral β-arylamines by asymmetric hydrogenation
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WingPhos, a C2-symmetric bisphosphorus ligand with a deep and well-defined chiral pocket was developed. It has shown high efficiency in the rhodium-catalyzed asymmetric hydrogenation of (E)-β-aryl-N-acetyl enamides, cyclic β-aryl enamides, and heterocyclic β-aryl enamides. A series of chiral β-arylisopropylamines, 2-aminotetralines, and 3-aminochromans can be synthesized with excellent ee values (nbd=3,5-norbornadiene; TON=turnover number). Copyright
- Liu, Guodu,Liu, Xiangqian,Cai, Zhihua,Jiao, Guangjun,Xu, Guangqing,Tang, Wenjun
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supporting information
p. 4235 - 4238
(2013/05/08)
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- One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes through a catalytic tandem reaction using an amino acid lithium salt
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One-pot asymmetric synthesis of γ-nitroaldehydes from aldehydes and nitroalkanes was achieved by a catalytic tandem reaction using a primary amino acid lithium salt, O-tert-butyldiphenylsilyl l-tyrosine lithium salt, as a catalyst. Various aryl, alkenyl, and alkyl aldehydes were converted into γ-nitroaldehydes via in situ generation of nitroalkenes.
- Yoshida, Masanori,Kitamikado, Naoki,Ikehara, Hiroto,Hara, Shoji
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experimental part
p. 2305 - 2309
(2011/06/11)
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- New rearrangement of conjugated cyclic ene nitroso O-trimethylsilyl acetals: Convenient synthesis of dihydro-2H-pyran-3-one and dihydrofuran-3-one oximes
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The nucleophile-induced rearrangement of cyclic N-alkoxy-N-(silyloxy) enamines was investigated. As a result, a new strategy for the synthesis of β-pyranone and β-furanone derivatives from nitro compounds is suggested. Georg Thieme Verlag Stuttgart New Yo
- Tabolin, Andrey A.,Khomutova, Yulia A.,Nelyubina, Yulia V.,Ioffe, Sema L.,Tartakovsky, Vladimir A.
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supporting information; experimental part
p. 2415 - 2422
(2011/09/20)
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- Alkenes from alcohols by tandem hydrogen transfer and condensation
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A ruthenium-catalysed oxidation of alcohols by hydrogen transfer has been coupled with organocatalysed condensations using pyrrolidine or piperidine, to give α,β-unsaturated esters and nitroalkenes. Reactions proceed with high (E)-selectivity and provide an efficient and straightforward route to α,β-unsaturated compounds.
- Hall, Michael I.,Pridmore, Simon J.,Williams, Jonathan M. J.
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supporting information; experimental part
p. 1975 - 1978
(2009/08/07)
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- An efficient synthesis of (E)-nitroalkenes catalyzed by recoverable diamino-functionalized mesostructured polymers
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A clean, efficient, and simple method has been developed for synthesis of (E)-nitroalkenes using FDU-ED as an efficient catalyst. The reactions proceeded with moderate to high yields (60-96%) under mild conditions. The catalyst FDU-ED is recyclable and can be reused more than seven times without significant loss of activity and selectivity.
- Yan, Shaoyu,Gao, Yuan,Xing, Rong,Shen, Yali,Liu, Yueming,Wu, Peng,Wu, Haihong
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p. 6294 - 6299
(2008/09/21)
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- Solvent-free nucleophilic addition of N-alkylhydroxylamines to substituted nitroolefins: Formation of nitrones by a tandem process
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Nucleophilic addition of 1-methyl-2-arylethylhydroxylamine to substituted β-nitrostyrene under solvent-free conditions has led to unexpected nitrones via a tandem process involving 1,4-addition and elimination. Copyright Taylor & Francis Group, LLC.
- Amutha, Chinnadurai,Muthusubramanian, Shanmugam
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p. 328 - 337
(2008/04/01)
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- A convenient procedure for the synthesis of 3-substituted 5,6-dihydro-4H-1,2-oxazines from nitroethane
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A novel and efficient four-step procedure for the synthesis of C-3-functionalised 5,6-dihydro-4H-1,2-oxazines from nitroethane is described. It includes preparation of 3-methyl-substituted six-membered cyclic nitronates, 3-(bromomethyl)-substituted 5,6-dihydro-4H-1,2-oxazines as intermediates, and nucleophilic substitution of bromine. Total yields of the target C-3-functionalised oxazines are 15-30% from nitroethane. Georg Thieme Verlag Stuttgart.
- Sukhorukov, Alexey Yu.,Klenov, Michael S.,Ivashkin, Pavel E.,Lesiv, Alexey V.,Khomutova, Yulya A.,Ioffe, Sema L.
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- Borrowing hydrogen: Iridium-catalysed reactions for the formation of C-C bonds from alcohols
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Alcohols have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The 'borrowed hydrogen' is then returned to the alkene to form a C-C bond. The Royal Society of Chemistry 2006.
- Black, Phillip. J.,Cami-Kobeci, Gerta,Edwards, Michael G.,Slatford, Paul A.,Whittlesey, Michael K.,Williams, Jonathan M. J.
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p. 116 - 125
(2007/10/03)
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- Catalytic activity of aminopropyl xerogels in the selective synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes
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Various aminopropyl-functionalized silicas (APS) were prepared by the sol-gel technique using different tetraethyl orthosilicate/ aminopropyltriethoxysilane (TEOS/ATS) ratios and tested as base catalysts for the nitroaldol reaction. The solids were fully characterized. It was proved that the amount of organic component strongly influences the composition and textural properties of the hybrid organic-inorganic materials. In particular, when ATS was increased to more than 40%, pore volume collapse was observed and a significant decrease in interaction with benzaldehyde reagent was revealed by FT-IR. Catalytic activity in the nitroaldol reaction was correlated with chemical composition and textural properties, suggesting that the catalyst efficiency depends on accessibility to the catalytic sites. In all cases, (E)-nitrostyrene was selectively obtained.
- Sartori,Bigi,Maggi,Sartorio,Macquarrie,Lenarda,Storaro,Coluccia,Martra
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p. 410 - 418
(2007/10/03)
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- A Nitro-Hunsdiecker Reaction: From Unsaturated Carboxylic Acids to Nitrostyrenes and Nitroarenes
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(Formula Presented) The nitrodecarboxylation of aromatic α,β-unsaturated carboxylic acids and ring-activated benzoic acids can be achieved using nitric acid (3 equiv) and catalytic AIBN (2 mol %) in MeCN. From the effect of various additives, the nitrodecarboxylation is postulated to involve the generation of an acyloxy radical RCO2? by a NO3? radical followed by attack of a NO2? radical.
- Das, Jaya Prakash,Sinha, Pradipta,Roy, Sujit
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p. 3055 - 3058
(2007/10/03)
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- Supported organic catalysts: Synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes over propylamine supported on MCM-41 silica as a reusable catalyst
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MCM-41-supported propylamine showed high catalytic efficiency in the nitroaldol condensation between nitroalkanes and aromatic aldehydes.
- Demicheli, Giuseppina,Maggi, Raimondo,Mazzacani, Alessandro,Righi, Paolo,Sartori, Giovanni,Bigi, Franca
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p. 2401 - 2403
(2007/10/03)
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- Asymmetric reduction of nitroalkenes with baker's yeast
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Various α,β-disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of α,β-disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield.
- Kawai, Yasushi,Inaba, Yoshikazu,Tokitoh, Norihiro
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p. 309 - 318
(2007/10/03)
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- An efficient enantioselective synthesis of (R,R)-formoterol, a potent bronchodilator, using lipases
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The potent β2-adrenergic receptor agonist formoterol (R,R)-1 has been obtained in enantiomerically pure form by a convenient chemoenzymatic approach by coupling of epoxide (R)-6 with the unprotected primary amine (R)-9. Both chiral precursors have been prepared by enantiodifferentiation processes involving Pseudomonas cepacia (lipase PS) and Candida antarctica lipase (CALB), respectively. For the resolution of amine 9, we have found that utilization of triethylamine as non-reactive base enhances the reaction rate and the enantioselectivity of the process. The key coupling reaction of (R)-6 and (R)-9 has been conducted through derivatization of the amine with the labile trimethylsilyl group, which liberates the amino group of the resulting amino alcohol (R,R)-11 upon column chromatography purification. In this way, the overall approach is shorter than others previously described. Copyright (C) 2000 Elsevier Science Ltd.
- Campos, Francisco,Bosch, M. Pilar,Guerrero, Angel
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p. 2705 - 2717
(2007/10/03)
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- Morpholine adsorbed on silica gel: A novel and mild basic catalyst for the synthesis of α,β-unsaturated nitroalkenes
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Syntheses of α,β-unsaturated nitroalkenes have been carried out under mild condition using morpholine adsorbed on silica gel as a novel catalyst.
- Bandgar, Babasaheb P.,Uppalla, Lav S.,Sadavarte, Vaibhav S.
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p. 949 - 952
(2007/10/03)
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- Zeolite as base catalyst: Nitroaldolic condensation
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The use of heterogeneous catalysts in producing petrochemicals and fine chemicals is one of the most successful lines in catalysis research. They may replace dangerous, corrosive, or toxic catalysts in some cases. The use of zeolites as main catalysts in petrochemical cracking reactions and in oil processing is a case of specific importance. The activity and selectivity of alkaline Y and X zeolites in promoting the nitroaldolic condensation of aromatic aldehydes with nitroalkanes affording nitroalkenes were studied. The reaction was promoted by the intrinsic basicity of the zeolites that increased with increases in both the aluminum content in the framework and the radius of the counter cation. The zeolite cages were microreactors, the walls of which were the basic sites whose number and strength could be controlled by choosing the chemical composition. The activity of substituted benzaldehyde revealed the influence of electronic effects. Steric factors played a critical role regarding the nitroalkanes; the combined effect of shape selectivity and basicity had to be considered in the heterogeneous nitroaldolic condensation.
- Ballini, Roberto,Bigi, Franca,Gogni, Elena,Maggi, Raimondo,Sartori, Giovanni
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p. 348 - 353
(2007/10/03)
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- Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents
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Polymer-supported reagents and other solid sequestering agents may be used to generate an array of 1,2,3,4-tetra-substituted pyrrole derivatives without any chromatographic purification step.
- Caldarelli, Marina,Habermann, Joerg,Ley, Steven V.
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p. 107 - 110
(2007/10/03)
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- Photochemical nitration by tetranitromethane. Part XLII. Photolysis of some 4-methoxystyrene derivatives with tetranitromethane
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The photochemical reaction of 4-methoxystyrene (2a) with tetranitromethane in dichloromethane gives the nitro-trinitromethyl adduct, 2-(4′-methoxyphenyl)-1-nitro-2-trinitromethylethane (1), which on chromatography on silica gel yields the (E)-nitroalkene, (E)-4′-methoxy-2-nitrostyrene (3); in acetonitrile solution adduct 1 is also the major product together with minor adducts. Similar reaction of trans-1-(4′-metrioxyphenyl)-1-propene (2b) in dichloromethane gives exclusively the stereoisomeric nitro-trinitromethyl adducts, 1-(4′-methoxyphenyl)-2-nitro-1-trinitromethylpropanes 6 and 7, but in acetonitrile adduct 7 is the major product together with a small amount of adduct 6 and a mixture of minor adducts. The base-catalysed reactions of adducts 1 and 6 gave nitroalkenes (E)-4′-methoxy-2-nitrostyrene (3) and (E)-1-(4′-methoxyphenyl)-2-nitro-1-propene (8), respectively, but reaction of adduct 7 gave a product of unknown structure. Kinetic studies of the base-catalysed reactions of nitro-trinitromethyl adducts 1, 6 and 7, and a nitro-trinitromethyl adduct derived from naphthalene, cis-1-nitro-4-trinitromethyl-1,4-dihydronaphthalene, are reported. A mixture of (E)- and (Z)-4-methoxycinnamonitrile did not react on extended photolysis with tetranitromethane. The photochemical reactions of 4-methoxystyrenes 2a and 2b with tetranitromethane are assumed to proceed via a radical chain reaction mechanism. Acta Chemica Scandinavica 1998.
- Eberson, Lennart,Hartshorn, Michael P.,Persson, Ola
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p. 745 - 750
(2007/10/03)
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- Microwave-Assisted Henry Reaction: Solventless Synthesis of Conjugated Nitroalkenes
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In a solventless system and under microwave irradiation, nitroalkanes react with arylaldehydes in the presence of a catalytic amount of ammonium acetate to afford, in one step, conjugated nitroalkenes without the isolation of intermediary β-nitro alcohols. - Key Words: Arylaldehydes; Nitroalkanes; Ammonium acetate; Conjugated nitroalkenes; Henry reaction; Microwave irradiation
- Varma, Rajender S.,Dahiya, Rajender,Kumar, Sudhir
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p. 5131 - 5134
(2007/10/03)
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- Synthesis of Phenylpyrrolylpyrroles. Part III
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Several ethyl 3-[(3-aryl-4-methyl)-2(1H)-pyrrolyl]-4-methyl-1H-pyrrole-2-carboxylates have been synthesized using two successive ethyl isocyanide addition-cyclizations to the appropriate nitropropene derivatives.
- Dumoulin,Rault,Robba
-
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- The yeast-mediated reduction of nitrostyrenes in organic solvent systems
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A range of nitrostyrenes have been reduced with dried baker's yeast in an organic solvent system. It was found that the reduction proceeded smoothly to give the corresponding nitroalkanes in good yield and with higher efficiency than the corresponding aqueous reaction system. No evidence for reduction of the nitro group was observed. In the case of β-methyl nitrostyrenes, racemic mixtures were formed, and it was shown that this is not due to racemization of the product.
- Bak, Radoslaw R.,McAnda, Anita F.,Smallridge, Andrew J.,Trewhella, Maurie A.
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p. 1257 - 1260
(2007/10/03)
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- Electrochemical Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes in Dimethyl Sulfoxide
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Electrochemical debromination reactions of erythro-dl-1-aryl-1,2-dibromo-2-nitropropanes 1a-d at a platinum electrode have been investigated by cyclic voltammetry in 0.10 M LiClO4/DMSO.The reactions produced (E)-1-aryl-2-nitropropenes 2a-d in high yields.The cyclic voltammograms were irreversible and the reduction current decrease as the number of cycles increased.The peak potential for the reductions waves are in the range of -0.51 to -0.56 V (vs Ag/Ag(1+)) and show no clear trend with different aryl substituent.The current density increased as the concentration of the substrate increased.The slopes of the plots of log(I/A) vs log are close to unity, indicating unimolecular processes.For all reactions, the Tafel slopes are in the range of 115-125 mV.The logarithm of the ratio iX/iH at -0.16 V did not correlate with the Hammett substituent constants.From these results, the mechanism of these reactions is assessed.
- Cho, Bong Rae,Cho, Eun Jeong,Lee, Seung Jae,Chae, Won Seok
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p. 2077 - 2081
(2007/10/02)
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- Mechanism of Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes Promoted by Secondary Amines in Acetonitrile
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Debromination reactions of erythro-dl-1-aryl-1,2-dibromo-2-nitropropanes with secondary amines in MeCN have been investigated kinetically.Reactions of erythro-dl-1-aryl-1,2-dibromo-2-nitropropanes with secondary amines in MeCN are stereospecific, producing (E)-1-aryl-2-nitropropenes quantitatively.The rate equation for the reaction is kobs = k2 + k32, indicating that the reactions proceed by both uncatalyzed and base-catalyzed pathways.The Hammett ?, Broensted β, ΔH(excit.), and ΔS(excit.) values for the k2 and k3 processes are 1.22 +/- 0.04 and 1.20 +/- 0.02, 0.77 +/- 0.05 and 1.05 +/- 0.13, 5.6 +/- 0.3 and 1.7 +/- 0.1 kcal/mol, and -49.1 +/- 4.5 and -60.7 +/- 204 eu, respectively.For dehalogenation reactions from vicinal dibromo and bromochloro compounds, the element effect of the leaving group kBr/kCl = 7.8 and 25 have been determined for the k2 and k3 processes.From these results, the mechanism and the trasition-state character of these reactions are assessed.
- Cho, Bong Rae,Lee, Sup Joo,Kim, Yong Kwan
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p. 2072 - 2076
(2007/10/02)
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- An improved synthesis of conjugated nitroolefins
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β-Nitro alcohols 1 react with triphenylphosphine/carbon tetrachloride/triethylamine under reflux to give the corresponding nitroolefins 2 in good yields (80-95%). Other groups such as tertiary hydroxyl, ether, halide etc. remain unaffected, and the nitroolefins so produced are exclusively the (E)-isomers.
- Saikia,Barua,Sharma,Ghosh
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p. 685 - 686
(2007/10/02)
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- HENRY CONDENSATION UNDER HIGH PRESSURE. 2. EFFECT OF AROMATIC ALDEHYDE TYPE AND PRESSURE ON THE YIELD OF ω-NITROSTYRENES AND SECONDARY PROCESSES
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Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily ω-nitrostyrenes (Ia, b) - (XXa, b) and small quantities of nitriles (Ic) - (XXc), oximes (Id) - (XXd), and ketones (Ie, f) - (XXe, f).The yields of (Ia, b) - (XXa, b) at P = 1 atm are higher for acceptor substitutents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents.High pressures suppress the formation of (Ic-f) - (XXc-f) and the Z-isomers of (Ia, b) - (XXa, b).The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b) - (XXa, b) which are intermediates in the synthesis of the psychotropic β-phenylethylamines.
- Agafonov, N. E.,Sedishev, I. P.,Dudin, A. V.,Kutin, A. A.,Stashina, G. A.,Zhulin, V. M.
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p. 366 - 372
(2007/10/02)
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- A Highly Chemoselective Reduction of Conjugated Nitro Olefins with Hantzsch Ester in the Presence of Silica Gel
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An effective system to reduce conjugated nitro olefins into the corresponding nitroalkanes is described.The system composed Hantzsch ester (HEH) and silica gel in benzene exerts high yield and excellent chemoselectivity under almost neutral conditions.Facile applications of the system to the syntheses of natural products are also described.
- FUJI, Masayuki
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p. 4029 - 4036
(2007/10/02)
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- NITRATION SUBSTITUTED STYRENES WITH NITRYL IODIDE
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Nitration of substituted styrenes by nitryl iodide, followed by treatment of the product with triethylamine, gives β-nitrostyrenes in good yield.
- Sy, Wing-Wah,By, Arnold W.
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p. 1193 - 1196
(2007/10/02)
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