59807-91-9

Upstream product

• 78839-96-0 (E/Z)-pent-1-enyl phenyl sulfide 
• 930-69-8 sodium thiophenolate 
• 26593-47-5 1,1,-dichloro-1-pentene 
• 3922-27-8 1,1,1-trichloropentane 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 
• 123-72-8 butyraldehyde 
• 3112-85-4 methylphenylsulfonate 

Downstream Products

• 621-27-2 3-n-propylphenol 
• 1363721-89-4 (2R)-2-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)pentyl phenyl sulfone 
• 1363721-99-6 (2S)-2((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)pentyl phenyl sulfone 

Relevant academic research and scientific papers

A base-controlled regioselective synthesis of allyl and vinyl phenyl sulfones

A reaction of diethyl phenylsulfonylmethylphosphonate with 2-arylacetaldehydes in the presence of a catalytic excess of sodium hydride (1.1 equiv) yields allyl phenyl sulfones in excellent yield under mild reaction conditions. In contrast, when less than 1 equiv of sodium hydride (0.90 equiv) is used, the corresponding vinyl phenyl sulfones are obtained exclusively. The vinyl phenyl sulfones can be completely converted to allyl phenyl sulfones with only 0.2 equiv of NaH, suggesting that the second hydride involvement in the above transformation is catalytic. The regioselective control observed in these reactions offers a general method for synthesizing novel vinyl and allyl phenyl sulfones in one step from the same starting materials. The regioselectivity and stereoselectivity of this reaction, however, are not maintained when 2-alkylacetaldehydes are reacted with diethyl phenylsulfonylmethylphosphonate under identical reaction conditions. Our results indicate that an extended conjugation of the double bond in allylsulfones formed from the reaction of 2-arylacetaldehydes is required for the observed regio- and stereoselectivity.

A useful method for configuration assignement of vinyl sulfides; stereochemical reassessment of the radical addition of benzenethiol to alkynes

A comparative analysis of the 1H NMR spectra of (E)- and (Z)-phenyl and alkyl sulfides and their corresponding sulfones provides a useful method for establishing their configuration.Although by employing this method we generally confirm our previous configurational assignement for benzenethiol/alkyne adducts, those for (E)- and (Z)-3-(phenylsulfanyl)hex-3-ene and 4-phenylsulfanyl)oct-4-ene, are shown to have been assigned incorrectly.In the light of the present results it is concluded that radical addition of benzenethio to alkynes at 100 deg C generally proceeds with trans-selectivity.This conclusion is the reverse of our earlier claim for the effect that benzenethiol adds to terminal alkynes and alkylphenylacetylenes in a trans-stereoselective mode, but in a cis-stereoselective mode to dialkylacetylenes bearing (rather) bulky alkyl groups.