908858-01-5

Basic information

• Product Name: (R_S,S)-N-(1-phenylethyl)-(p-nitrophenylsulfinyl)acetamide
• Synonyms: (R_S,S)-N-(1-phenylethyl)-(p-nitrophenylsulfinyl)acetamide
• CAS NO: 908858-01-5
• Molecular Weight: 332.38
• Mol File: 908858-01-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R_S,S)-N-(1-phenylethyl)-(p-nitrophenylsulfinyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R_S,S)-N-(1-phenylethyl)-(p-nitrophenylsulfinyl)acetamide(908858-01-5)
• EPA Substance Registry System: (R_S,S)-N-(1-phenylethyl)-(p-nitrophenylsulfinyl)acetamide(908858-01-5)

Safety Data

• Hazardous Substances Data: 908858-01-5(Hazardous Substances Data)

Upstream product

• 75032-27-8 ethyl <(p-nitrophenyl)thio>acetate 
• 3406-75-5 2-(4-nitrophenylthio)acetic acid 
• 908858-12-8 (S)-N-(1-phenylethyl)-(p-nitrophenylthio)acetamide 

Relevant articles and documents

Highly stereoselective asymmetric pummerer reactions that incorporate intermolecular and intramolecular nonbonded S...O interactions

New chiral sulfoxides (RS,S)-3, (SS,S)-3, (R S,S)-4, and (SS,S)-4 and known chiral sulfoxides (R S)-5, (RS)-6, and (RS)-7 were synthesized, and the stereochemistry of the new sulfoxides (RS,S)-3 and (R S,S)-4 was determined by X-ray crystallographic analysis. In their crystallographic structures, the intramolecular nonbonded S...O close contacts were recognized. Analyses of several sulfoxide complexes including rac-11 with N,N-dimethylacetamide (DMAC) or N-methyl-2-pyrrolidone (NMP) in a MeOH solution utilizing cold-spray ionization mass spectrometry provided, for the first time, direct information for intermolecular nonbonded S...O interactions between sulfoxides and amide (or lactam) in a solution. Highly diastereoselective and enantioselective Pummerer reactions based on the concept of intermolecular and intramolecular nonbonded S...O interactions were performed by treatment of several chiral sulfoxides (RS, S)-3, (SS, S)-3, (RS, S)-4, (SS, S)-4, (R S)-5, (RS)-6, and (RS)-7 with acetic anhydride and trimethylsilyl triflate (TMSOTf) in DMAC, NMP, N,N-dimethylformamide, and N-formylpiperidine. Mechanistic studies on these facile stereoselective Pummerer reactions revealed the necessity for the amide/TMSOTf complex, such as 26 or 27, to be an efficient activation reagent for Ac2O and a trapping reagent for the released acetate ion, and that DMAC and NMP had a positive effect on this highly stereoselective chiral transfer reaction.