77527-88-9Relevant articles and documents
Mild and efficient α-chlorination of carbonyl compounds using ammonium chloride and oxone (2KHSO5·KHSO4· K2SO4)
Swamy, Peraka,Kumar, MacHarla Arun,Reddy, Marri Mahender,Narender, Nama
supporting information; experimental part, p. 432 - 434 (2012/06/01)
A simple protocol for the α-monochlorination of ketones and 1,3-dicarbonyl compounds utilizing NH4Cl as a source of chlorine and Oxone as an oxidant in methanol without catalyst is presented. The reaction proceeds at ambient temperature in yields ranging from moderate to excellent.
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.
