Sulfonylimino group transfer reaction using imino-λ3-iodanes with I2 as catalyst under metal-free conditions
A new practical procedure of imination for sulfide has been developed. The treatment of (N-tosylimino)-phenyl-λ3-iodane, PhINTs, with various sulfides in the presence of a catalytic amount of I2 under metal-free conditions affords the corresponding N-tosylsulfilimine compounds with moderate to good yields. This facile transfer procedure of the sulfonylimino group can also be applied to triphenylphosphine to produce the respective iminotriphenylphosphoranes in high yields. According to the reaction mechanism studies, the process of imination from (N-tosylimino)-phenyl-λ3-iodane to sulfide under the conditions may involve radical steps within the reaction mechanism.
Yoshimura, Akira,Makitalo, Cody L.,Jarvi, Melissa E.,Shea, Michael T.,Postnikov, Pavel S.,Rohde, Gregory T.,Zhdankin, Viktor V.,Saito, Akio,Yusubov, Mekhman S.
(2019/03/19)
A simple method for the preparation of N-sulfonylsulfilimines from sulfides
While excellent methods exist for the oxidation of sulfides to sulfoxides R1R2S → R1R2SO, the aza-version of this atom transfer redox process, i.e., R1R2S → R1R2S=N-SO
Marzinzik,Sharpless
p. 594 - 596
(2007/10/03)
Hypervalent iodine in synthesis XXXII: A novel way for the synthesis of N-sulfonylsulfilimines from sulfides and sulfonamides using iodosobenzene diacetate
A number of N-sulfonylsulfilimines have been prepared through a novel way for the reaction of iodosobenzene diacetate with sulfides and sulfonamides under mild conditions.
Ou, Wei,Chen, Zhen-Chu
p. 4443 - 4449
(2007/10/03)
PREPARATION OF TETRAALKYLAMMONIUM N-CHLORO-p-TOLUENESULFONAMIDES AND THEIR APPLICATION TO IMINATION OF PHOSPHORUS COMPOUNDS AND SULFIDES.
Tetraalkylammonium N-chloro-p-toluenesulfonamides were prepared from chloramine T and tetraalkylammonium chlorides as a substance corresponding to anhydrous chloramine T, and found to give rise to the effective tosylimination of phosphorus compounds and d
Yamamoto,Yoshida,Hojyo,Terauchi
p. 3341 - 3342
(2007/10/02)
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