The reaction of 2-phenyl substituted four, five and six membered thiacycloalkanes (1, 4 and 7) with lithium and a catalytic amount of DTBB (5 mol%) in THF at− 78° C leads to the corresponding sulphur-containing benzylic organolithium compounds (2, 5 and 8), which by reaction with different electrophiles [D2O, Me3SiCl, ButCHO, Me2CO, Et2CO,(CH2) 4CO, CO2] followed by hydrolysis with water afford the expected functionalised mercaptans (3, ...
