26818-06-4Relevant academic research and scientific papers
Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids
Davies, Jacob,Janssen-Müller, Daniel,Zimin, Dmitry P.,Day, Craig S.,Yanagi, Tomoyuki,Elfert, Jonas,Martin, Ruben
supporting information, p. 4949 - 4954 (2021/04/07)
A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.
Cis-Dioxomolybdenum(VI) complexes with unsymmetric linear tetradentate ligands: Syntheses, structures and bromoperoxidase activities
Kurapati, Sathish Kumar,Pal, Samudranil
, p. 116 - 124 (2016/02/18)
Reactions of [MoO2(acetylacetonate)2], 2-((2-(2-hydroxyethylamino)ethylamino)methyl)-4-R-phenols (H2Ln, n = 1-5 for R = H, Me, OMe, Cl and Br, respectively) and KOH in 1:1:2 mole ratio in methanol afford a series of complexes having the general formula cis-[MoO2(Ln)] (1, 2, 3, 4, 5) in 81-86% yields. The complexes have been characterized using elemental analysis, spectroscopy (infrared, UV-visible, and 1H NMR, 13C NMR and 13C-DEPT NMR) and electrochemical measurements. The molecular structures of 1, 2, 3, 4 have been determined using single-crystal X-ray crystallography. In each of 1, 2, 3, 4, the ONNO-donor 6,5,5-membered fused chelate rings forming (Ln)2- and the two mutually cis oxo groups assemble a distorted octahedral N2O4 coordination sphere around the metal centre. In the crystal lattice, each of 1, 2, 3, 4 forms a one-dimensional infinite chain structure via intermolecular N-H...O hydrogen bonding interactions. In cyclic voltammograms, the diamagnetic complexes display an irreversible metal-centred reduction in the potential range -0.73 to -0.88 V (vs Ag/AgCl). The physicochemical data are consistent with a very similar gross molecular structure for all of 1, 2, 3, 4, 5. All the complexes exhibit decent bromoperoxidase activities and are also able to effectively catalyse benzoin and methyl(phenyl)sulfide oxidation reactions.
Chemo- And stereodivergent preparation of terminal epoxides and bromohydrins through One-Pot biocatalysed reactions: Access to enantiopure Five- and Six-Membered N-Heterocycles
Bisogno, Fabricio R.,Cuetos, Anibal,Orden, Alejandro A.,Kurina-Sanz, Marcela,Lavandera, Ivan,Gotor, Vicente
supporting information; experimental part, p. 1657 - 1661 (2010/09/18)
Different enantiopure terminal epoxides or bromohydrins have chemoselectively been synthesised in one-pot starting from the corresponding a-bromo ketones through alcohol dehydrogenase (ADH)-catalysed processes adding an organic cosolvent and tuning appropriately the medium pH and the temperature. Thus, at neutral pH enantiopure bromohydrins were obtained while using basic conditions (pH 9.5-10) epoxides were isolated as the main product. Furthermore, by simple selection of the biocatalyst, chemo- and stereodivergent transformations were achieved to obtain, e.g., enantiopure prolinol or piperidin-3-ol.
Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
Patil, Rajendra D.,Joshi, Girdhar,Adimurthy, Subbarayappa,Ranu, Brindaban C.
experimental part, p. 2529 - 2532 (2009/09/06)
A new method for the preparation of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent has been developed. Several α-bromoketones were successfully prepared from a variety of olefins by this method. This procedure is an alternative to conventional molecular bromine.
Comparative study of the vicinal functionalization of olefins with 2:1 bromide/bromate and iodide/iodate reagents
Agrawal, Manoj K.,Adimurthy, Subbarayappa,Ganguly, Bishwajit,Ghosh, Pushpito K.
experimental part, p. 2791 - 2797 (2009/08/08)
A comparative evaluation was made on the syntheses of vicinal halohydrins, halo methyl ethers, and halo acetates from olefins using 2:1 Br-/BrO3- and I-/IO3- reagents. In many cases both reagents afforded products selectively in high yields. The highest halogen atom efficiencies attained were 97% and 93% for Br-/BrO3- and I-/IO3-, respectively. Of the two reagents, I-/IO3- was established to be the preferred reagent for vicinal functionalization of linear alkenes and also for halo acetate preparation. However, only Br-/BrO3- was effective for vicinal functionalization of trans-stilbene and chalcones.
Conversion of alkyl halides into the corresponding alcohols under mild reaction conditions
Ruddick, Clare L.,Hodge, Philip,Houghton, Mark P.
, p. 1359 - 1362 (2007/10/03)
Reaction of primary, cyclopentyl, allyl and arylmethyl halides, but not an acyclic secondary halide or a tertiary halide, in acetone or tetrahydrofuran with the formate form of a commercial anion exchange resin gave formate esters in good yields. The formates were hydrolysed efficiently to the corresponding alcohols by a brief treatment with hydrochloric acid. Reaction of primary alkyl bromides or iodides, secondary alkyl bromides, cinnamyl and arylmethyl halides in tetrahydropyran or 1,4-dioxane with the bicarbonate form of the same anion-exchange resin gave the corresponding alcohols directly in good yields. This latter reaction can be carried out successfully in the presence of ester or amide groups.
Solvation and Steric Effects on Electrophilic Reactivity of Ethylenic Compounds. Part 4. Bromination of Oct-1-ene in Anionic Microemulsions
Ruasse, Marie-Francoise,Blagoeva, Iva B.,Krys, Sophie,Sebastian-Gambaro, Maria-Angela
, p. 1283 - 1289 (2007/10/02)
The kinetics and product distribution of the bromination of oct-1-ene in anionic sodium dodecylsulfate (SDS)-butanol-hexane-water and sodium bis(2-ethylhexyl)sulfosuccinate (AOT)-isooctane-water microemulsions are reported.Dibromide and solvent-incorporated products are formed.In both kinds of microemulsion, the dibromide yield decreases smoothly from 100percent to 10percent as the water content of the reaction medium increases from 0percent to 65percent, whereas in pure water or butanol it is greater than 80percent.The regioselectivity of the water- or butanol-incorporated products is 70:30 Markownikoff: anti-Markovnikoff, a ratio identical with that found in pure methanol, butanol or water.Kinetic bromide-ion effects on the reaction in a water-rich (75percent) SDS microemulsion, show that bromination occurs in the interfacial oil-water region, and not in one of the two microphases, the only brominating agent being molecular bromine and not the tribromide ion.The overall bromination rate constant in this SDS microemulsion (k = 1.6 * 104 dm3 mol-1 s-1) is smaller than that in pure water (2.3 * 107 dm3 mol-1 s-1) and in SDS micelles (2 * 105 dm3 mol-1 s-1), in the same range as that in a 80-20 methanol-water mixture, and greater than that in butanol (2 * 102 dm3 mol-1 s-1).These results are discussed in terms of the particular characteristics (ionization and dissociating abilities, aquation and water properties) of the microemulsion interfaces.
Micellar Effects upon Alkene Bromination. 2. The Role of Alkene Hydrophobicity
Cerichelli, Giorgio,Grande, Celeste,Luchetti, Luciana,Mancini, Giovanna
, p. 3025 - 3030 (2007/10/02)
Surface polarity of cettyltrimethylammonium bromide (CTAB) aqueous micelles was checked by use of as a probe the bromination reaction of a series of 1-alkenes and a water-soluble alkene, cis-4-cyclohexene-1,2-dicarboxylic acid dimethyl ester (I).There was
ORGANIC SYNTHESIS WITH SULPHONES - XVII. THE ANTI-MARKOWNIKOFF HALOSULPHONYLATION OF OLEFINS VIA AN IONIC PATHWAY, AND A NEW METHOD OF PREPARING BENZENESULPHONYL IODIDE
Harwood, L. M.,Julia, M.,Thuillier, G. Le
, p. 2483 - 2487 (2007/10/02)
Iodine and bromine in the presence of sodium benzenesulphinate react with olefins in acetone solution to give halosulphones resulting from an apparent steric direction of attack at the intermediate halonium ion.A straightforward preparation of benzenesulphonyl iodide from benzenesulphonyl chloride and sodium iodide is also described.
