22690-22-8Relevant articles and documents
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.
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.
