68602-14-2

Upstream product

• 583-03-9 1-Phenyl-1-pentanol 
• 109-72-8 n-butyllithium 

Downstream Products

• 105494-90-4 C₁₇H₂₀O₂S 
• 105494-84-6 1-phenyl-1-phenylsulphonyl-1-trimethylsilylpentane 
• 77815-48-6 1-phenyl-1-phenylthio-1-trimethylsilylpentane 
• 1009-14-9 phenyl butyl ketone 

Relevant academic research and scientific papers

Halogen-lithium exchange versus deprotonation: regioselective mono- and dilithiation of aryl benzyl sulfides. A simple approach to α,2-dilithiotoluene equivalents

Halogen-lithium exchange and deprotonation reactions between aryl benzyl sulfides and alkyllithiums were investigated. The resultant mono- and dilithiated intermediates were converted into the corresponding aldehydes and boronic, or carboxylic acids in good yields. It was found that diethyl ether stabilizes the ortho-lithiated compounds toward isomerisation to the benzylic derivatives. The process occurs easily in THF at low temperature and is a facile route to the α,2-dilithiotoluene derivative which can be transformed into a dicarboxylic acid on treatment with CO2.