22690-22-8Relevant academic research and scientific papers
Ionic liquid as reagent. A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions
Ranu, Brindaban C.,Banerjee, Subhash
, p. 4517 - 4519 (2007/10/03)
A variety of structurally diverse epoxides undergo facile cleavages by ionic liquid, [AcMIm]X without any catalyst and solvent to produce the corresponding vicinal halohydrins in high yields. The cleavages are considerably fast and highly regioselective.
Regio- and Stereoselective Synthesis of β-Halohydrins from 1,2-Epoxides with Ammonium Halides in the Presence of Metal Salts
Chini, Marco,Crotti, Paolo,Gardelli, Cristina,Macchia, Franco
, p. 3805 - 3812 (2007/10/02)
A simple efficient, stereoselective, and regioselective method for the synthesis of β-chlorohydrins, β-bromohydrins, and β-iodohydrins by the direct opening of 1,2-epoxides with the corresponding ammonium halide in acetonitrile, in the presence of metal salts, is described.This new method appears to be of general use and competitive with the other methods previously reported.
Proprietes nucleophiles des carbenoides monohalogenes non fonctionnels
Villieras, J.,Kirschleger, B.,Tarhouni, R.,Rambaud, M.
, p. 470 - 478 (2007/10/02)
The coupling of non functionalised monohalocarbenoids R1-CXLi-R2 1 (R1 = alkyl, H ; R2 = H, CH3) with carbonyl compounds at -115 degree leads to the formation of lithium salts of halohydrins which readily give epoxides (via lithium halide elimination) at -95 degree in the presence of lithium bromide.The regiospecific synthesis of α-haloketones and α-haloaldehydes can be achieved by acylation of 1 with esters.A total lack of reactivity of 1 towards powerful alkylating electrophiles has been observed showing that they are not nucleophilic organometallics.The reactivity with carbonyl compounds seems to be promoted by the carbonyl-lithium (from the carbenoid) complexation.A correlation between nucleophilic/electrophilic properties of carbenoids (mono-, di- and trihalo-) and their assigned structure (metallocarbenium halides) is discussed.
MONOHALOMETHYLLITHIUM XCH2Li : STABILIZATION OF A POTENTIAL SYNTHETIC REAGENT
Tarhouni, R.,Kirschleger, B.,Rambaud, M.,Villieras, J.
, p. 835 - 838 (2007/10/02)
The preparation of monohalomethyllithium XCH2Li is achieved by Bromine-lithium exchange from the corresponding Bromohalomethane in the presence of one equivalent of lithium bromide at -110 degC in THF-Ether-Pentane solutions.This reagent, on coupling with various carbonyl compounds leads to halohydrins, epoxides and α-halomethyl ketones with high yields.
