96-13-9Relevant academic research and scientific papers
Crystal structure, characterization, Hirshfeld surface analysis and DFT studies of two [propane 3-bromo-1-(triphenyl phosphonium)] cations containing bromide (I) and tribromide (II) anions: The anion (II) as a new brominating agent for unsaturated compounds
Nokhbeh, Seyed Reza,Gholizadeh, Mostafa,Salimi, Alireza,Sparkes, Hazel A.
, p. 542 - 554 (2019/06/18)
In this study, propane 3-bromo-1- (triphenyl phosphonium) bromide, I, and propane 3-bromo-1- (triphenyl phosphonium) tribromide, II, (II as a new brominating agent) were synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT-IR, spectroscopy, Thermogravimetric Analysis, Differential thermal analysis, Differential scanning calorimetry and single crystal X-ray analysis. Density functional theory calculations (energy, structural optimization and frequencies, Natural Bond Orbital, absorption energy and binding energy) were performed by using B3LYP/6-311 G++ (d, p) level of theory. Hirshfeld surface analysis and fingerprint plots were utilized to investigate the role of bromide and tribromide anions on the crystal packing structures of title compounds. The results revealed that the change of accompanying anionic moiety can affect the directional interactions of C-H?Br hydrogen bonds between anionic and cationic units in which the H?Br with a proportion of 53.8% and 40.9% have the major contribution in the stabilization of crystal structures of I and II, respectively. Furthermore, the thermal stability of new brominating agent II with tribromide anion was compared with compound I with bromide anion. Nontoxicity, short reaction time, thermal stability, simple working up and high yield are some of the advantages of these salts.
One-Pot Strategy for Thiazoline Synthesis from Alkenes and Thioamides
Alom, Nur-E,Wu, Fan,Li, Wei
supporting information, p. 930 - 933 (2017/02/26)
A convenient synthesis of a privileged pharmaceutical motif, thiazoline is accomplished. This reaction utilizes simple and readily available alkene and thioamide substrates in an intermolecular fashion via a simple one-pot procedure. A wide range of functional groups is tolerated, and the thiazoline product has been further utilized for the synthesis of the corresponding β-aminothiol and thiazole from routine hydrolysis and oxidation protocols.
Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-Anverene
Seidl, Frederick J.,Burns, Noah Z.
supporting information, p. 1361 - 1365 (2016/08/02)
The scope of a recently reported method for the catalytic enantioselective bromochlorination of allylic alcohols is expanded to include a specific homoallylic alcohol. Critical factors for optimization of this reaction are highlighted. The utility of the
Bromination of olefins with HBr and DMSO
Karki, Megha,Magolan, Jakob
, p. 3701 - 3707 (2015/04/22)
A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.
Bromination of alkenols with the H2O2 - LiBr - CeIII and H2O2 - LiBr - CeIV systems
Nikishin,Sokova,Kapustina
, p. 459 - 463 (2013/07/05)
Reactions of alkenols with H2O2 - LiBr - Ce(NO 3)3·6H2O or H2O2 - LiBr - Ce(NH4)2(NO3)6 system led to bromination of the double bond to yield vicinal dibromoalkanols. The reaction proceeded highly selectively, no oxidation of the hydroxyl group virtually occurred.
A combination of in vivo selection and cell sorting for the identification of enantioselective biocatalysts
Fernandez-Alvaro, Elena,Snajdrova, Radka,Jochens, Helge,Davids, Timo,Boettcher, Dominique,Bornscheuer, Uwe T.
supporting information; experimental part, p. 8584 - 8587 (2011/11/07)
The "carrot and stick" principle could be combined with cell sorting to enable the selection of enantioselective esterase variants from a mutant library. Hence, the enormous diversity generated in directed evolution experiments is now easily accessible by this high-throughput system. In line with the principle, the hydrolysis of 1 glycerin supports cell growth, whereas the hydrolysis of 2 leads to cell death. Copyright
Monobromoborane-dimethyl sulfide - A highly promising reagent for the regio- and chemoselective brominative cleavage of terminal epoxides into vicinal bromohydrins
Roy, Chandra D.,Brown, Herbert C.
, p. 139 - 145 (2008/02/11)
Monobromoborane?dimethyl sulfide (BH2Br?SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at ?25°C, 4-chlorobenzaldehyde still underwent 12?13% reduction of an aldehydic group. CSIRO 2007.
Dimethoxyboron bromide - A new, efficient, regio- and chemoselective reagent for the conversion of terminal epoxides into bromohydrins
Roy, Chandra D.,Brown, Herbert C.
, p. 639 - 641 (2007/10/03)
Dimethoxyboron bromide, (MeO)2BBr, easily prepared in excellent yield from boron tribromide and trimethyl borate, is a new, efficient, regio- and chemoselective reagent useful for the halogenative cleavage of compounds containing epoxy groups into vicinal bromohydrins in the presence of ether, acetal, ketal, N-oxide, and sulfoxide groups, at low temperatures (-78°C).
Poly(vinylpyrrolidone)-bromine complex; a mild and efficient reagent for selective bromination of alkenes and oxidation of alcohols
Lakouraj, Moslem Mansour,Tajbakhsh, Mahmood,Mokhtary, Masoud
, p. 481 - 483 (2007/10/03)
Poly(vinylpyrrolidone)-bromine complex (PVP-Br2) is easily prepared and used as a mild and convenient reagent for selective bromination of alkenes and at the position α-hydrogen of active carbonyl compounds. Selective oxidation of benzylic alcohols in the presence of aliphatic alcohols were also achieved at room temperature.
NaIO4-Mediated Selective Oxidative Halogenation of Alkenes and Aromatics Using Alkali Metal Halides
Dewkar, Gajanan K.,Narina, Srinivasarao V.,Sudalai, Arumugam
, p. 4501 - 4504 (2007/10/03)
(Equation presented) NaIO4 oxidizes alkali metal halides efficiently in aqueous medium to halogenate alkenes and aromatics and produce the corresponding halo derivatives in excellent regio and stereoselectivity. The system also demonstrates the asymmetric version of bromo hydroxylation using β-cyclodextrin complexes, resulting in moderate ee.
