19324-69-7Relevant academic research and scientific papers
Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone
MacHarla, Arun Kumar,Chozhiyath Nappunni, Rohitha,Nama, Narender
supporting information; experimental part, p. 1401 - 1405 (2012/04/04)
An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.
Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes
De Almeida, Leonardo S.,Esteves, Pierre M.,De Mattos, Marcio C. S.
, p. 1515 - 1518 (2007/10/03)
A simple one-step method for the preparation of tribromoisocyanuric acid in good yield (87%) has been developed. The reaction of tribromoisocyanuric acid with alkenes in presence of nucleophilic solvents (MeOH, i-PrOH, AcOH and a mixture of H2O-acetone, 1:5) led to the corresponding β-bromoethers, β-bromoacetates and bromohydrins, in high regioselectivity and good yields (73-98%). Georg Thieme Verlag Stuttgart.
A New Regioselective Synthesis of Vicinal Bromohydrins via Free Radical Decarboxylative Bromination of β-Hydroxycarboxylic Acids
Greb, Marco,Hartung, Jens
, p. 69 - 72 (2007/10/03)
Diisopropylcarbodiimide-mediated condensations between N-hydroxypyridine- 2(1H)-thione and β-hydroxycarboxylic acids afforded mixed anhydrides which were regioselectively converted into vicinal bromohydrins under neutral conditions.
N-BENZOYLCARBAMATE CYCLIZATIONS
Knapp, Spencer,Kukkola, Paivi J.,Sharma, Shashi,Pietranico, Sherrie
, p. 5399 - 5402 (2007/10/02)
The anion of an alcohol derived N-benzoylcarbamate may be used to deliver nitrogen intramolecularly to electrophilic centers.This allows the stereocontrolled synthesis of a variety of amino-alcohol and amino-diol derivatives.
CONVERSION OF EPOXIDES TO BROMOHYDRINS BY B-BROMOBIS(DIMETHYLAMINO)BORANE
Bell, Thomas W.,Ciaccio, James A.
, p. 827 - 830 (2007/10/02)
Reaction of the title reagent with 1-alkene oxides regioselectively yields the corresponding 1-bromo-2-alkanols, while the more substituted bromide predominates in the cases of styrene oxide and 1-methylcyclohexene oxide.
Use of Polymeric Phosphine-Halogen Complexes in the Conversion of Epoxides to Halohydrins
Caputo, Romualdo,Ferreri, Carla,Noviello, Silvana,Palumbo, Giovanni
, p. 499 - 501 (2007/10/02)
Polystyryldiphenylphosphine-halogen complexes are convenient reagents for converting epoxides to halohydrins under mild and non-acidic conditions.The method requires only a filtration and evaporation process for product isolation.
DILITHIUM TETRABROMONICKELATE (II) AS A SOURCE OF SOFT NUCLEOPHILIC BROMIDE: REACTION WITH EPOXIDES
Dawe, Robert D.,Molinski, Tadeusz F.,Turner, John V.
, p. 2061 - 2064 (2007/10/02)
Dilithium tetrabromonickelate (II) in THF serves as a source of "soft" nucleophilic bromide and reacts regioselectively with epoxides to give bromohydrins in high yield.
A NEW GENERAL SYNTHESIS OF HALOHYDRINS
Palumbo, Giovanni,Ferreri, Carla,Caputo, Romualdo
, p. 1307 - 1310 (2007/10/02)
A new synthetic method has been devised for the rapid conversion of epoxides to chloro-, bromo- and iodo-hydrins in quantitative yield, under mild conditions and in the absence of protic acids.
