83187-71-7

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 13307-75-0 (phenylthio)methyllithium 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 108-98-5 thiophenol 
• 10290-42-3 1-diazo-4-phenyl-2-butanone 

Downstream Products

• 206278-54-8 (Z)-1,5-Diphenyl-2-phenylsulfanyl-pent-1-en-3-one 
• 1261152-67-3 2-oxo-4-phenyl-1-(phenylthio)butyl acetate 
• 206278-61-7 (Z)-(R)-1-Phenyl-4-phenylsulfanyl-non-4-en-3-ol 
• 206278-55-9 (Z)-1-Phenyl-4-phenylsulfanyl-non-4-en-3-one 

Relevant academic research and scientific papers

One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents

Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.

Enantioselective synthesis of α-hydroxy thioesters via oxazaborolidine- mediated reduction of α-phenylthio enones

α-Phenylthio-α,β-alkenones (2), readily available by Pd(II)-catalysed coupling of (E)-1 phenylthio-1-tributylstannylhex-1-ene with the corresponding acid chlorides have been treated with borane in the presence of phenylglycine- or proline-derived oxazaborolidines to afford 2-phenylthio-2- alken-1-ols (3) with good to excellent enantioselectivities. Ozonolysis of 3 provides a new and efficient route to chiral α-hydroxy thioesters 4.

REGIOSPECIFIC SYNTHESIS OF α-(PHENYLTHIO)KETONES VIA RHODIUM(II) ACETATE CATALYSED ADDITION OF THIOPHENOL TO α-DIAZOKETONES

αα-Addition of thiophenol to α-diazoketones is catalysed efficiently by rhodium(II) acetate in benzene solution at room temperature, offering a convenient regiospecific route to a variety of α-(phenylthio)ketones.