51351-89-4Relevant academic research and scientific papers
A simple synthesis of some new arylsulfonylnitromethanes
Aleksiev,Ivanova,Valeva
experimental part, p. 743 - 747 (2012/06/18)
Arylsulfonylnitromethanes were obtained by a nucleophilic substitution reaction. The suggested method of obtaining arylsulfonylnitromethanes has some important advantages over the methods known so far: It is a relatively short, one-stage process; no byproducts are obtained, so there is no need for further procedures to separate the main products from thereaction mixture; and the final compounds possess a good degree of purity. The structure of the new products were confirmed by 1H NMR, IR, and elemental analysis. The solid state structure of 6 was established by X-ray analysis. Copyright
Sulfonyl Esters. V. A Preparation of Dichloromethyl Sulfones
Langler, Richard Francis,Steeves, Jennifer Lea
, p. 1641 - 1646 (2007/10/02)
α-Sulfonyl methyl esters have been chlorinated in the presence of base.Chlorination proceeds with accompanying demethoxycarbonylation to furnish dichloromethyl sulfones in good yields.
Pathways in the Reactions of Nitronate Ions with Sulphonyl Halides
Pigou, Paul E.,Stirling, Charles J. M.
, p. 725 - 730 (2007/10/02)
Primary and tertiary nitronate ions and sulphonyl bromides and iodides rapidly equilibrate with the nitrohalides and sulphinate ion.Products are determined by solvent and by the occurence of cross-equilibrum reactions, some of which have single-electron-transfer mechanism.The reaction of arene-sulphinate and thiolate ions with 1,2-dibromo-2-nitro-1-phenylethane gave E-β-nitrostyrene by Z-philic elimination in both cases, but the more basic thiolate ion also gave, by protophilic elimination, 2-bromo-2-nitro-1-phenylethene.
Bromonitromethane. A Versatile Electrophile
Fishwick, Brian R.,Rowles, David K.,Stirling, Charles J. M.
, p. 1171 - 1180 (2007/10/02)
Pathways in reactions of bromonitromethane with a variety of nucleophiles have been investigated.With thiolates, the electrophilic centre is bromine and the initial products are disulphides.When the thiolate ion itself carries an electrophilic centre such as carbonyl or cyano β-to sulphur, the product is a nitrothiophene derived from subsequent reaction of the first-formed disulphide with nitronate ion displaced in the initial process.This provides a generalisation of earlier nitrothiophene synthesis by this route.In reactions with arenesulphinate ion, the electrophilic centre is also bromine and equilibration between the initial reactants and the initial products, sulphonyl bromide and nitronate ion, is established.The components of the equilibrium subsequently react either with each other or with the solvent.Reactions with sulphides are slow and distal substituents such as hydroxy- or cyano- so much reduce reactivity that no reaction is observed.Dimethyl sulfide attacks bromonitromethane at the carbon atom,and subsequent attack on the nitromethyl sulphonium salt initially formed gives methylthionitromethane and trimethylsulphonium bromide.Iodide ion attacks at bromine to give iodine, presumably via iodine bromide, but with tervalent phosphorus nucleophiles, attack is at oxygen giving the corresponding oxides and HCN in a double deoxygenation sequence.For hydroxide, methoxide and hydride ions (from sodium borohydride), nucleophilic attack is at hydrogen and the nitronate ion produced is inert to further attack.There is no evidence of carbene formation by α-elimination.When the anion of bromonitromethane is allowed to react with tributylboron, the anionic migration-displacement which follows boron-carbon bond formation, yields 1-nitropentane.The anion of bromonitromethane is unreactive towards aldehydes and electrophilic alkenes.
Silyl Nitronates in Organic Synthesis. Routes to Heterocycles and Cyclopentanoids. Synthesis of Allethrolone and Calythrone. Acylation and Cyanohydroxylation of Double Bonds. An Exploratory Study
Andersen, Soeren H.,Das, Nalin B.,Joergensen, Ruth D.,Kjeldsen, Gunhild,Knudsen, Jes S.,et al.
, p. 1 - 14 (2007/10/02)
Silyl nitronates are versatile reagents for the preparation of heterocycles by dipolar addition to double bonds.The intermediate isoxazolidines can be transformed to 2-isoxazolines, isoxazoles, furans, dihydrofuranones, pyrazoles, pyridazines and pyridazones.Reduction of 2-isoxazolines with Ti3+ leads to hydroxylated 1,4-diketones, which subsequently can be cyclized to cyclopentenones.Routes to calythrone, rethrolones, prostanoids and a number of naturally occurring dihydrofuranones are devised, as well as synthetic procedures for acylation, preparation of endiones, hydroxyacylation, cyanation and hydroxycyanation of double bonds.
Aryl dibromonitromethyl sulfones
-
, (2008/06/13)
Aryl dibromonitromethyl sulfones, new compounds, wherein aryl is phenyl or lower alkyl phenyl, are effective as antimicrobials at a concentration of about 100 parts per million.
