- Modular Regiospecific Synthesis of Nitrated Fatty Acids
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Endogenous nitrated fatty acids are an important class of signaling molecules. Herein a modular route for the efficient and regiospecific preparation of nitrooleic acids as well as various analogues is described. The approach is based on a simple set of alkyl halides as common building blocks and a Henry reaction/Burgess dehydration sequence for the formation of the key nitroalkene moiety.
- Hock, Katharina J.,Grimmer, Jennifer,G?bel, Dominik,Gasaya, George Gichogo T.,Roos, Jessica,Maucher, Isabelle V.,Kühn, Benjamin,Fettel, Jasmin,Maier, Thorsten J.,Manolikakes, Georg
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p. 615 - 636
(2017/01/25)
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- Easy and direct conversion of tosylates and mesylates into nitroalkanes
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Tosylates and mesylates were directly converted into the corresponding nitroalkanes, by their treatment with tetrabutylammonium nitrite (TBAN) under mild conditions.
- Palmieri, Alessandr,Gabrielli, Serena,Ballini, Roberto
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p. 533 - 536
(2013/04/24)
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- Sequential continuous flow processes for the oxidation of amines and azides by using HOF·MeCN
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The generation and use of the highly potent oxidising agent HOF·MeCN in a controlled single continuous flow process is described. Oxidations of amines and azides to corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Oxidation in flow: The oxidation of amines and azides to the corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Copyright
- McPake, Christopher B.,Murray, Christopher B.,Sandford, Graham
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experimental part
p. 312 - 319
(2012/06/15)
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- PROCESS FOR MAKING AND USING HOF.RCN
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The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.
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Page/Page column 7
(2011/04/14)
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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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- The first conversion of primary alkyl halides to nitroalkanes under aqueous medium
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Primary nitroalkanes and α,ω-dinitroalkanes can be easily obtained in aqueous medium by reaction of the corresponding halo derivatives with silver nitrite. The procedure works well with both alkyl bomide and alkyl iodide and proceeds in satisfactory to good yields even in the presence of other functionalities, minimizing the formation of the undesired alkyl nitrites.
- Ballini, Roberto,Barboni, Luciano,Giarlo, Guido
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p. 6907 - 6908
(2007/10/03)
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- From azides to nitro compounds in a few seconds using HOF·CH3CN
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HOF·CH3CN, a very efficient oxygen-transfer agent, was reacted with various azides to form the corresponding nitro compounds in excellent yields and in very short reaction times. The respective nitroso derivatives were found to be intermediates in this reaction. When the azides were reacted with MCPBA or DMDO, no reaction took place, and the starting materials were fully recovered. Copyright
- Rozen, Shlomo,Carmeli, Mira
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p. 8118 - 8119
(2007/10/03)
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- Dimethyldioxirane Oxidation of Primary Amines
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Several primary amines 2 have been oxidized with dimethyldioxirane (1) nder a variety of conditions.Mixtures of dimeric nitrosoalkanes 4 and oximes 5 were typically obtained with solutions of the oxidant in excess.In several instances, nitrones 12 were found as byproducts in these reactions.In situ oxidations using oxone in buffered aqueous solutions also gave nitrosoalkanes 4 and oximes 3 as important products; in addition, oxaziridines 11 were obtained in significant amounts in biphasic procedures containing methylene chloride.The corresponding nitroalkanes 5 were not formed in major amounts in either oxidation procedures, unless large excesses of oxidant were used.These results are discussed in terms of several competing processes which occur under the different reaction conditions.
- Crandall, Jack K.,Reix, Thierry
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p. 6759 - 6764
(2007/10/02)
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- Preparation of carboxylic acids from salts of nitroketones
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A method of preparing carboxylic acids is provided by contacting an ammonium, Group IA or Group IIA metal salt of a nitroketone in an aqueous medium. The method is preferably undertaken in the presence of an acidic mineral acid salt.
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