97273-03-5

Basic information

• Product Name: 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid
• Synonyms: 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid
• CAS NO: 97273-03-5
• Molecular Weight: 265.376
• Mol File: 97273-03-5.mol

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid(97273-03-5)
• EPA Substance Registry System: 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid(97273-03-5)

Safety Data

• Hazardous Substances Data: 97273-03-5(Hazardous Substances Data)

Upstream product

• 97273-00-2 2-Cyclohexylamino-2-phenylethansulfonsaeure 
• 4091-26-3 β-styrenesulfonyl chloride 
• 108-91-8 cyclohexylamine 
• 167280-05-9 2-Cyclohexyl-4,4-dimethyl-3-phenyl-[1,2]thiazetidine 1,1-dioxide 
• 2039-44-3 sodium 2-phenylethylenesulfonate 

Downstream Products

• 208395-41-9 2-Cyclohexyl-3-phenyl-4,4-bis-trimethylsilanyl-[1,2]thiazetidine 1,1-dioxide 
• 13719-46-5 (E)-N-cyclohexyl-2-phenylethenesulfonamide 
• 21573-69-3 1-phenyl-1-cyclopentanecarboxaldehyde 
• 176696-63-2 (E)-2-Phenyl-1-trimethylsilanyl-ethenesulfonic acid cyclohexylamide 
• 56753-71-0 phenyl-propene-2-sulfonic acid amide 
• 64984-09-4 (E)-(2-phenylethenyl)sulfonamide 
• 210300-80-4 (E)-1-(tert-Butyl-dimethyl-silanyl)-2-phenyl-ethenesulfonic acid cyclohexyl-methyl-amide 
• 167280-05-9 2-Cyclohexyl-4,4-dimethyl-3-phenyl-[1,2]thiazetidine 1,1-dioxide 

Relevant articles and documents

Preparation of sulfonamides from sodium sulfonates: Ph3P·Br2 and Ph3P·Cl2 as a mild halogenating reagent for sulfonyl bromides and sulfonyl chlorides

Arene- and alkanesulfonamides were prepared by treatment of the corresponding sodium sulfonates with triphenylphosphine dibromide or dichloride followed by amines in the presence of triethylamine via sulfonyl halides. Reactions of sodium aminosulfonates gave cyclized products. Amidation of p-toluenesulfonic acid with triphenylphosphine dichloride was also examined to give N-benzyl-p-toluenesulfonamide. Methyl p- toluenesulfonate was obtained by esterification of sodium p-toluenesulfonate via p-toluenesulfonyl chloride.

Reactions of 1,2-thiazetidine 1,1-dioxides with organometallics: β- elimination and N-S bond cleavage

Reactions of 4-nonsubstituted β-sultams 1 with methyllithium gave only (E)-vinylsulfonamides 2, whereas 2-aminoethyl sulfones 3 were obtained as minor products by use of methylmagnesium bromide. Reactions of 4- monosubstituted β-sultams 6 with organolithiums gave (E)-vinylsulfonamides 7 stereoselectively regardless of the configuration of 3- and 4-substituents. Treatment of 4,4-dimethyl-β-sultam 8a with methylmagnesium bromide and methyllithium provided 2-aminoethyl sulfone 9 and bis-sulfone 10, respectively, and isopropyl phenyl sulfone 11 was obtained by use of phenyllithium or phenylmagnesium bromide.

Synthesis and Structure of 2,3-Disubstituted 1,2-Thiazetidine 1,1-Dioxides

2-Alkylamino-2-phenylethanesulfonic acids 3 are prepared from sodium 2-phenylethenesulfonate (2).Compounds 3 are chlorinated and cyclized to yield the title compounds 5.Their structures are characterized by IR and NMR spectroscopy and compared to those of analogous β-lactams.An X-ray analysis of the β-sultam 5d establishes the proposed structure.