Rapid conversion of hindered arylsulfonates to alkyl chlorides with retention of configuration.
Arylsulfonates of hindered secondary alcohols are converted to the corresponding alkyl chlorides very rapidly and in good yields in the presence of titanium tetrachloride at low temperatures. These reactions proceed with exclusive retention of configuration.
Lepore
Salvatore D
SD
Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431-0991, USA. slepore@fau.edu
Bhunia
Anjan K
AK
Mondal
Deboprosad
D
Cohn
Pamela C
PC
Lefkowitz
Craig
C
D000478:Alkylation; D001190:Arylsulfonates / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D013997:Time Factors; D014025:Titanium / Q000737:chemistry
D001190:Arylsulfonates; D002712:Chlorides; D004952:Esters; C025096:titanium tetrachloride; D014025:Titanium