A simple nitration of electrophilic alkenes with tetranitromethane in the presence of triethylamine. Synthesis of functionalized β-nitroalkenes (original) (raw)
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Reactions of sugar nitro-alkenes with acetoacetic esters
Carbohydrate Research, 1984
3,4,5,6,7-Penta-O-actyl-l,2-dideoxy-l-nitro-D-gluco-hept-l-enitol reacts with methyl acetoacetate in an unusual Michael reaction, giving the normal adduct (6), and a bicyclic derivative (9) that arises from quasi-dimerization of the former when a high concentration of the base is used. Acetylation of compound 9 gives the hydroxylamine O-acetate (10).
Reactions of sugar nitro-alkenes with 3-aminocrotonic esters
Carbohydrate Research, 1984
3,4,5,6,7-Penta-O-acetyl-l,2-dideoxy-l-nitro-D-gluco-and -D-g&cto-hept-lenitol and 3,4,5,6-tetra-O-acetyl-l,2-dideoxy-l-nitro-D-xylo-hex-l-enitol react with 3-aminocrotonic esters, yielding mixtures of the epimeric Michael adducts. These are thermally stable, and do not cyclize to pyrroles. The structures, configurations, and conformations of these compounds were established on the basis of their spectroscopic and X-ray crystallographic data. The intramolecularly bonded, (2) configuration was deduced for all of them. Mild hydrolysis of adducts with acid yields the corresponding 2-(nitromethylpolyacetoxyalkyl)acetoacetates.
Canadian Journal of Chemistry, 1982
The reactions of 1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-carboxaldehyde (1), 1-oxyl-2,2,5,5-tetramethyl-3-cyano-3-pyrroline (2), ethyl 1-oxy(-2,2,5,5-tetramethyl-3-pyrroline-3-carbonyl carbonate (3), and N-(1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-carbonyl)imidazolide (4) are investigated with several nucleophiles (dialkylcadmium, diethyl sodio-malonate, magnesium enolate of ethyl hydrogen malonate, nitromethane-anion) to obtain α,β-unsaturated ketones, β-ketoesters, or conjugated reaction products. Aldehyde 1 is reacted with several methyl ketones (acetylmethylene-triphenylphosphorane, acetophenone, 2-acetylpyridine, 4-phenyl-3-butyn-2-one) to give spin labeled polyenones. The reaction of 4-(1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-yl)-2-buten-2-one (24a) with ethylenediamine gives 7,14-bis-(1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-yl)-5,12-dimethyl-1,4,8,11-tetraazatetradeca-7,14-diene biradical (25).
The Journal of Organic Chemistry, 1996
The asymmetric variant of the tandem [4 + 2]/[3 + 2] cycloaddition of nitroalkenes with chiral vinyl ethers has been extensively explored in recent years. 1 To date, the chiral vinyl ethers that have been utilized in the tandem sequence are derived from bornane-2,3-diol, 1, trans-2phenylcyclohexanol, 2, and 2,2-diphenylcyclopentanol, 3, . These auxiliaries have served admirably in many aspects of the cycloaddition process, but some limitations still exist, such as the following: (1) length of synthesis, (2) low selectivity in exo mode cycloadditions or (3) unavailability in both enantiomeric series.
Nitrocompounds as useful reagents for the synthesis of dicarbonyl derivatives
Arkivoc, 2006
The reaction of functionalized nitroalkanes with electrophiles such as Michael acceptors and aldehydes is one of the most exploited procedures for the synthesis of new carbon-carbon bonds. Conversion of the nitro group in the adduct into a carbonyl derivative usually provides a rapid entry to dicarbonyl systems that are amenable to further synthetic transformation into a plethora of important targets. oxidative, reductive, as well as almost neutral, conditions. The aim of this review is to discuss the utilization of nitroalkanes as nucleophilic reagents for the synthesis of dicarbonyl derivatives using a strategy involving a nucleophilic addition of the nitro derivative followed by a nitro to carbonyl conversion. Although these procedures are usually accomplished by a two-step synthesis, there are several examples in which this overall transformation can be carried out in a 'one-pot' system thus realizing a more efficient process.
Selected reductions of conjugated nitroalkenes
Tetrahedron, 1990
Conjugated nitroalkenes are readily reduced by a variety of borane and borohydride reagents. The reactions provide a convenient access to a number of nitrogen and oxygen based functional groups.