98061-54-2

Upstream product

• 504-31-4 pyran-2-one 
• 19978-32-6 3-bromo-2H-pyran-2-one 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 

Downstream Products

• 141553-93-7 benzyl 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-exo-carboxylate 
• 141510-35-2 benzyl 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate 
• 141510-33-0 5-endo-acetyl-4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene 
• 141553-92-6 methyl 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-exo-carboxylate 
• 141510-34-1 methyl 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-endo-carboxylate 
• 141510-38-5 (5R,6R,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-1-oxo-6-p-tolylsulfanyl-2-oxa-spiro[4.5]dec-7-ene-6-carboxylic acid methyl ester 
• 141510-37-4 (5R,6R,9S)-9-Hydroxy-1-oxo-6-p-tolylsulfanyl-2-oxa-spiro[4.5]dec-7-ene-6-carboxylic acid methyl ester 
• 141510-31-8 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-endo-carboxaldehyde 
• 141553-94-8 methyl 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-endo-methyl-5-exo-carboxylate 
• 141510-36-3 methyl 4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene-5-exo-methyl-5-endo-carboxylate 
• 141510-30-7 5-endo-cyano-4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene 
• 141553-88-0 5-exo-cyano-4-(4'-methylbenzenesulfenyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-ene 
• 99268-86-7 (+/-)-3-p-toluenesulfinyl-2-pyrone 
• 99268-87-8 3-(p-toluenesulfonyl)-2-pyrone 

Relevant academic research and scientific papers

3-Cuprio-2-pyrone: An Extraordinary Organocopper Reagent

3-Cuprio-2-pyrone (1) was prepared via Scheme I and was treated with a very wide variety of typically SN2- and SN1-reactive substrates as well as with typical acyl electrophiles.The only substrates that reacted via pyrone transfer we

AN ORGANOMETALLIC ROUTE TO (+/-)-3-p-TOLUENESULFINYL-2-PYRONE

3-Bromo-2-pyrone reacts with dimethylcopperlithium and then with p-tolyl p-toluenethiosulfonate to form 3-p-toluenethio-2-pyrone.Organocopper species are likely intermediates in this reaction.Oxidation of the sulfide produces (+/-)-3-p-toluenesulfinyl-2-pyrone.The overall process involves an important and useful umpolung, a reversal of reactivity at C(3) of the pyrone ring from an electrophilic center to a nucleophilic center.