41747-39-1Relevant academic research and scientific papers
Solvolysis of 1-Aryl-2,2,2-trihalogenoethyl Toluene-p-sulphonates. Generation of Carbocations Destabilized by Trichloro- or Tribromo-methyl Groups
Lima, Carmem de,Santos, Isaias dos,Rosa, Sergio Mauro Cordova da,Rezende, Marcos Caroli
, p. 2099 - 2102 (2007/10/02)
The kinetics of solvolysis of the title compounds, leading to the formation of carbocations destabilized by a CCl3 or a CBr3 group, have been studied in various solvents.Destabilization by the CX3 group increases with the electronegativity of the halogen
Studies on the rearrangement of (trichloromethyl)carbinols to α-chloroacetic acids
Reeve, Wilkins,McKee, James R.,Brown, Robert,Lakshmanan, Sitarama,McKee, Gertrude A.
, p. 485 - 493 (2007/10/02)
Phenyl(trichloromethyl)carbinol undergoes an unimolecular, predominantly intramolecular conversion into potassium α-chlorophenylacetate on stirring with 10percent aqueous potassium hydroxide at 0 deg C for several days.Besides providing an interesting example of a 1-2 chlorine shift, the reaction is of potential importance for the synthesis of α-chloro acids.The study of a variety of (trichloromethyl)carbinols shows the reaction is general for secondary (trichloromethyl)carbinols as well as trichloroethanol.The mechanism of the reaction involves the preliminary formation of an epoxide.Several mechanisms are considered for the conversion of the epoxide to the α-chloroacetate anion, but none accounts for all of the experimental facts.Tertiary carbinols break down at the epoxide stage into a ketone and carbon monoxide.
