193537-12-1

Upstream product

• 100-68-5 methyl-phenyl-thioether 
• 538-51-2 benzylidene phenylamine 
• 13307-75-0 (phenylthio)methyllithium 

Downstream Products

• 4566-58-9 1,3-Diphenyl-3-phenylaminopropanol 
• 24723-59-9 syn-4,4-Dimethyl-1-phenyl-1-phenylaminopentan-3-ol 
• 24723-59-9 anti-4,4-Dimethyl-1-phenyl-1-phenylaminopentan-3-ol 
• 193537-28-9 1-N-Anilino-1-phenyl-4,4-dimethyl-pentan-3-ol 
• 779-54-4 phenyl(1-phenylethyl)amine 

Relevant academic research and scientific papers

Functionalized organolithium compounds of DTBB-catalyzed sulfur-lithium exchange

The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1,4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78°C leads to the formation of the corresponding β- or γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t- BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78°C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.

β-Functionalised organolithium compounds through a sulfur-lithium exchange

The successive reaction of different β-hydroxy or β-amino tbioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTB in THF at -78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, Bu(t)CHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between -78 and 20°C yields, after hydrolysis with water, the expected functionalised alcohols or amines 3aa-de in a regioselective manner.