- Synthesis and characterization of a novel nanomagnetic phase-transfer catalyst and its application to regioselective synthesis of β-azido and β-nitro alcohols in water
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Immobilization of polyethylene glycol-substituted 1-methylimidazolium bromide on the surface of magnetic Fe3O4 nanoparticles through hexane-1,6-diyldicarbamate linker afforded a powerful and reusable heterogeneous phase-transfer cata
- Ayashi,Fallah-Mehrjardi,Kiasat
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p. 846 - 852
(2017/08/02)
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- Synthesis and characterization of a novel nano-Fe3O4-copoly[(styrene/acrylic acid)/grafted ethylene oxide and its application as a magnetic and recyclable phase-transfer catalyst in the preparation of β-azido alcohols and β-nitro alc
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A facile method was developed for the synthesis of β-azido alcohols and β-nitro alcohols in the presence of a novel nano-Fe3O4-copoly[(styrene/acrylic acid)/grafted ethylene oxide (nano-Fe3O4-PS-Co-[PAA-g-PEG])
- Kiasat, Ali Reza,Daei, Mina,Saghanezhad, Seyyed Jafar
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p. 581 - 594
(2016/04/26)
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- Efficient kinetic bioresolution of 2-nitrocyclohexanol
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The kinetic bioresolution of 2-nitrocyclohexanol 1 was investigated by screening a range of hydrolases both for enantioselective transesterification and for enantioselective hydrolysis of the corresponding acetate. By appropriate choice of biocatalyst and conditions, both enantiomers of cis and trans 2-nitrocyclohexanol 1 can be accessed in enantiopure form.
- Milner, Sinead E.,Brossat, Maude,Moody, Thomas S.,Elcoate, Curtis J.,Lawrence, Simon E.,Maguire, Anita R.
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experimental part
p. 1011 - 1016
(2010/08/22)
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- Oxidation of azides by the HOF·CH3CN: A novel synthesis of nitro compounds
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The HOF·CH3CN complex, readily prepared by passing F 2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. It is unique in its capacity to oxidize various azides into the corresponding nitro derivatives. This method requires short reactions times and room temperature or below, and the desired nitro compounds were usually isolated in very good yields. The respective nitroso derivatives are believed to be the intermediates in this reaction. Functional groups such as aromatic rings, ketones, nitriles, halides, alcohols, and esters are tolerated. Sulfides react with HOF·CH3CN usually at the same rate as azides. Amines and olefins, however, react faster, so they have to be protected first. Nitro derivatives with various oxygen isotopes can be made using the labeled H 18OF·CH3CN. In the case of chiral azides the stereochemistry around the nitrogen-bonded carbons is retained.
- Carmeli, Mira,Rozen, Shlomo
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p. 4585 - 4589
(2007/10/03)
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- Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-, NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4
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Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN, N3-, NO3-, NO2, SCN, Br and Cl-, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN- is an easy procedure for the high yielding preparation of epoxy sulfides.
- Iranpoor, Nasser,Firouzabadi, Habib,Shekarize, Marzieh
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p. 724 - 727
(2007/10/03)
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- Synthesis of 2-nitroalcohols by regioselective ring opening of epoxides with MgSO4/MeOH/NaNO2 system: A short synthesis of immunosuppressive agent FTY-720
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It has been demonstrated that a variety of epoxides can easily be opened with a system consisting of MgSO4/MeOH/NaNO2 giving the corresponding 2-nitroalcohols in excellent yields. This strategy has been applied to achieve a short synthesis of Immunosuppressive Agent FTY - 720.
- Kalita,Barua,Bezbarua,Bez
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p. 1411 - 1414
(2007/10/03)
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- The aluminum amalgam reduction of 2-nitroalkanols promoted by ultrasound
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The sonochemical promoted aluminum amalgam reduction of 2-nitroalkanols provides an improved yield and accelerated conversion to the corresponding amino alcohols when compared to the nonultrasound (benchtop) reductions. The appearance of by-product hydrox
- Fitch, Richard W.,Luzzio, Frederick A.
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p. 6013 - 6016
(2007/10/02)
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- A new, highly efficient synthesis of conjugated nitrocycloalkenes
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Sodium borohydride reduction of α-nitrocycloalkanones and successive dehydration of the obtained β-nitroalkanols, by acetylation and dehydroacetylation with basic alumina/DMAP, in refluxing dichloromethane, affords, in one por procedure, conjugated nitrocycloalkenes.
- Ballini, Roberto,Palestini, Corrado
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p. 5731 - 5734
(2007/10/02)
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- Highly selective reduction of 2-nitrocycloalkanones to 2-nitrocycloalkanols with zinc borohydride in DME
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Clean and efficient reduction of 2-nitrocycloalkanones to 2-nitrocycloalkanols has been achieved using zinc borohydride in 1,2-dimethoxyethane.
- Ranu,Das
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p. 2361 - 2362
(2007/10/02)
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- A Practical Preparations of Conjugated Nitroalkenes
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Treatment of alkenes (1a-5a) with sodium nitrite and iodine in ethyl acetate (or ether) and water in the presence of ethylene glycol (or propylene glycol) provides conjugated nitroalkenes (1b-5b) in 49-82percent yields.
- Jew, Sang-sup,Kim, Hee-doo,Cho, Youn-sang,Cook, Chae-ho
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p. 1747 - 1748
(2007/10/02)
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- Reaction of Nitrogen Dioxide with Alkenes and Polyunsaturated Fatty Acids: Addition and Hydrogen Abstraction Mechanisms
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The reactions of nitrogen dioxide in a carrier gas (nitrogen, oxygen, or air) with cyclohexene and a series of mono-, di-, and trienes is reported at NO2 concentrations ranging from 70 ppm to 50percent.A complete product analysis was made with cyclohexene, and these data allow the calculation of the fraction of the NO2 that reacts by addition to the double bond or by abstraction of an allylic hydrogen.At high concentrations of NO2, addition is the predominant process, in agreement with the literature.However, below 10 000 ppm (1percent), hydrogen abstraction predominates.We suggest this is because of competition between a reversible addition and an irreversible H-abstraction step, much as is the case for the well-known bromine atom reaction system.In fact, a kinetic analysis shows that the ratios of rate constants for addition and abstraction are similar for both NO2 and the bromine atom.A less direct method (analysis of water formed) was used to estimate the addition to abstraction ratio for other alkenes and for esters of unsaturated fatty acids; these data are in agreement with the cyclohexene data.The autoxidation of unsaturated fatty acid esters initiated by NO2 also was studied, and kinetic chain lengths and autoxidizability ratios are given.
- Pryor, William A.,Lightsey, John W.,Church, Daniel F.
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p. 6685 - 6692
(2007/10/02)
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- α-NITRO KETONES 7 : SYNTHESIS OF CONJUGATED NITROCYCLOHEXENES
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The reduction of 2-nitrocyclohexanones to the 2-nitrocyclohexanols with sodium borohydride followed by treatment of the β-nitroalcohols with sodium hydride and subsequent acidification of the salts leads to the regioselective synthesis of conjugated nitrocyclohexenes from cyclohexanones.
- Dampawan, Pimchit,Zajac, Walter W.
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p. 135 - 138
(2007/10/02)
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