13719-46-5Relevant academic research and scientific papers
Selective C-N bond cleavage of 4-silyl-substituted 1,2-thiazetidine 1,1-dioxides with EtAlCl2: Stereospecific formation of (E)-vinylsulfonamides
Kataoka, Tadashi,Iwama, Tetsuo,Takagi, Atsuko
, p. 2257 - 2260 (1996)
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.
Solvent-free synthesis of novel styrenesulfonamide derivatives and evaluation of their antibacterial activity
Maghsoodi, Narjes Khaton,Khazaeli, Tooba,Massah, Ahmad Reza
, p. 141 - 144 (2015)
Novel N-aryl-styrenesulfonamide derivatives have been prepared from styrenesulfonyl chloride and a variety of amines under solvent-free conditions and their in vitro anti-bacterial activities against Staphylococcus aureus and Escherichia coli have been de
Desulfonylation-Initiated Distal Alkenyl Migration in Copper-Catalyzed Alkenylation of Unactivated Alkenes
Wang, Xiaoyang,Liu, Jing,Yu, Ze,Guo, Minjie,Tang, Xiangyang,Wang, Guangwei
, p. 6516 - 6519 (2018/10/20)
A novel and efficient protocol for desulfonylation-initiated distal alkenyl migration and its application to the elusive alkenylation of unactivated alkenes have been presented. This radical cascade process has successfully achieved the vicinal difluoroal
Stereospecific C-N bond cleavage of 4-silylated 1,2-thiazetidine 1,1- dioxides with EtAlCl2 or AlCl3: Formation of (E)-vinylsulfonamides
Iwama, Tetsuo,Takagi, Atsuko,Kataoka, Tadashi
, p. 757 - 766 (2007/10/03)
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
Iwama, Tetsuo,Kataoka, Tadashi,Muraoka, Osamu,Tanabe, Genzoh
, p. 5507 - 5522 (2007/10/03)
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.
