84072-32-2

Upstream product

• 67-56-1 methanol 
• 78-54-6 1,2-di(1-hydroxycyclohexyl)acetylene 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 5602-31-3 1,2-di-(1-acetoxy-1-cyclohexyl)ethyne 
• 108-94-1 cyclohexanone 
• 23528-44-1 1,2-bis-(phenylmercapto)ethylene 

Downstream Products

• 86001-25-4 rac-(S,S)-1,2-dicyclohexylethane-1,2-diol 
• 124-04-9 Adipic acid 
• 53723-48-1 1,1'-(1,2-ethanediylidene)biscyclohexane 
• 24434-24-0 1,2-bis[(1-hydroxy)cyclohexyl]ethane 

Relevant academic research and scientific papers

DTBB-catalysed lithiation of 1,2-bis(phenylsulfanyl)ethene: Does 1-lithio-2-phenylsulfanylethene really exist?

The reaction of (Z)- or (E)-1,2-bis(phenylsulfanyl)ethene (1) with an excess of lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 2.5 mol%) in the presence of a carbonyl compound as electrophile (Barbier conditions) in THF at -78°C leads, after hydrolysis with water at temperatures ranging between -78°C and rt, to a mixture of the corresponding (Z/E)-unsaturated 1,4-diols 2, the diastereomers ratio being independent of the stereochemistry of the starting materials. Allylic alcohols 3 are the main by-products, resulting from a lithium-hydrogen exchange on some of the lithiated intermediates along the whole process. A mechanistic explanation for the observed behaviour is given.