176696-63-2

Upstream product

• 167280-05-9 2-Cyclohexyl-4,4-dimethyl-3-phenyl-[1,2]thiazetidine 1,1-dioxide 
• 97273-03-5 2-Cyclohexyl-3-phenyl-1,2-thiazetidin-1,1-dioxid 
• 2211-66-7 N-phenyl(methylidene)cyclohexanamine 
• 208395-41-9 2-Cyclohexyl-3-phenyl-4,4-bis-trimethylsilanyl-[1,2]thiazetidine 1,1-dioxide 

Relevant academic research and scientific papers

Stereospecific C-N bond cleavage of 4-silylated 1,2-thiazetidine 1,1- dioxides with EtAlCl2 or AlCl3: Formation of (E)-vinylsulfonamides

Monosilylation of 1,2-thiazetidine 1,1-dioxides (β-sultams) 3 gave (3R*, 4S*)-4-monosilyl-β-sultams 4 stereoselectively. Disilylated β- sultams 5 were obtained by the use of trimethylsilyl chloride. Treatment of 4-monosilyl-β-sultams 4 with EtAlCl2 caused stereospecific C-N bond cleavage owing to β-cation stabilization of the silicon group to provide (E)-vinylsulfonamides (E)-7. (E)-α-Silylstyrylsulfonamides (E)-7j - l were generated in the reaction of 4,4-disilyl-β-sultams 5 with EtAlCl2. Reaction of 4-silyl-β-sultams with AlCl3 afforded N-dealkylated (E)- vinylsulfonamides in good yields. Reaction of (E)-α-silylstyrylsulfonamide (E)-10 with benzaldehyde in the presence of tetrabutylammonium fluoride and BF3·Et2O provided the allylic alcohol (E)-12.

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.

Selective C-N bond cleavage of 4-silyl-substituted 1,2-thiazetidine 1,1-dioxides with EtAlCl2: Stereospecific formation of (E)-vinylsulfonamides

Monosilylation of 1,2-thiazetidine 1,1-dioxides (β-sultams) furnished (3R*, 4S*)-4-silylated β-sultams stereoselectively. Treatment of 4-silylated β-sultams with a Lewis acid caused the selective C-N bod cleavage because of the β-silyl stabilization against the resultant carbenium ion followed by desilation to provide (E)-vinylsulfonamides stereospecifically.