102333-77-7Relevant academic research and scientific papers
ETUDE DE LA RECTIVITE D'YLURES DE SULFONIUM ET DE PYRIDINIUM STABILISES PAR UN GROUPEMENT CYANOFORMYLE.
Baudy-Floc'h, M.,Robert, A.
, p. 3297 - 3302 (2007/10/02)
The sulfonium and pyridinium ylides stabilized by a cyanoformyl group, in acidic medium, lead to sulfonium and pyridinium ketene salts.This originality has been used to prepare new stabilized ylides, or derivatives of substituted arylacetic acids or 4-hydroxy thiazoles.
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.
