58749-31-8

Upstream product

• 30134-12-4 phenyl 3-phenylpropyl sulfide 

Downstream Products

• 100946-88-1 (1S,3S,4R)-3-Phenethyl-2-thia-bicyclo[2.2.1]hept-5-ene 
• 100946-88-1 (1R,3S,4S)-3-Phenethyl-2-thia-bicyclo[2.2.1]hept-5-ene 
• 115120-16-6 Thioacetic acid S-(1-benzenesulfonyl-3-phenyl-propyl) ester 
• 115120-13-3 Thioacetic acid S-(3-phenyl-1-phenylsulfanyl-propyl) ester 

Relevant academic research and scientific papers

Diastereoselectivity in the Diels-Alder Reactions of Thioaldehydes

The Diels-Alder reaction of thioaldehydes with cyclopentadiene occurs with a preference for the endo isomer.The highest selectivity is observed for thioaldehydes RCHS where R is a bulky group such as tert-butyl or isopropyl.Thioaldehydes having α-alkoxy, acetoxy, or siloxy substituents also react with useful endo selectivity.Secondary orbital overlap is a small factor in these reactions since α-oxo thioaldehydes react with relatively low endo selectivity.Steric effects are primarily responsible for the endo preferences observed.The Diels-Alder reactions of chiral α-oxygen substituted thioaldehydes also occur with useful thioformyl face selectivity.A Cornforth transition state 5 is most likely for the selectivity observed for α-alkoxy or acetoxy thioaldehydes, but the α-hydroxy analogue 23 reacts with the opposite facial preference.The highest face selectivity is obtained with the acetonide of thioglyceraldehyde, generated by photolysis of the phenacyl sulfide 15b.