57872-24-9

Upstream product

• 1600-44-8 1-oxothiolane 
• 24698-06-4 S-p-nitrophenyl-S-phenyl-N-tosylsulfilimine 
• 13553-70-3 1,1,2,3,4,5-hexahydro-1-<<(4-methylphenyl)sulfonyl>imino>tiophene 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 1338062-05-7 4-methyl-N-[(2-propoxyphenyl)-λ³-iodanylidene]benzenesulfonamide 

Relevant academic research and scientific papers

O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates

Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic

Iodine(III)-Mediated Preparations of Nitrogen-Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State

Reaction of sulfonamides with iodosobenzene leads to phenyliodinanes. A new catalysis reaction of the decomposition of these products in the presence of sulfoxides that allows the smooth synthesis of sulfoximines has been evidenced and studied: copper(n) salts were used to prepare compounds 4a-j and 5b, d, f, j, k from the corresponding, easily prepared, sulfoxides. The reactions proceed with retention of configuration at the sulfur center, and copper(II) triflate is the best candidate for the catalyst for the imination. Switching from sulfonamides to sulfinamides in the preparation of the starting iodinanes completely alters the reaction pathway: iodinanes are no longer accessible, and sulfonimidates 7a-j are obtained instead. This behavior can be rationalized by the increase in pKa brought about by the removal of one oxygen atom from the sulfur center. Sulfonimidates are interesting molecules with varied applications. Optimization of their one-pot synthesis has been achieved by carrying out the reaction in acetonitrile. The stereochemical study has shown that the transformation proceeds with global retention of the configuration at the sulfur center, albeit with erosion of the enantiomeric purity. A model accounting for this outcome is proposed. In addition, the presence of oxidized sulfonamide by-products has been explained, and this latter pathway becomes the sole one when alcohol is replaced by water. Good yields of the oxidized products are obtained.

Catalytic synthesis of sulfoximines using copper(II) salts

The reaction of PhI=NTs with sulfoxides in the presence of catalytic amounts of copper(II) salts afforded the corresponding N-tosylsulfoximines in high yield. This method is highly tolerant to reaction conditions (no need of distilled solvents and/or iner

PEROXYACETIC ACID: A USEFUL COOXIDANT FOR THE RUTHENIUM TETROXIDE OXIDATION OF N-SULFONYLSULFILIMINES

The oxidation of a wide variety of N-sulfonylsulfilimines to the corresponding sulfoximines is described.The oxidation involves the use of peroxyacetic acid as a cooxidant for the actual oxidant, ruthenium tetroxide, in a biphasic media.

COPPER CATALYZED REACTIONS OF S,S-DIARYL-N-TOSYLSULFILIMINES WITH SULFOXIDES: NEW SYNTHESIS OF N-TOSYLSULFOXIMINES

S,S-Diaryl-N-tosylsulfilimines were readily reduced by treatment with copper to give the corresponding sulfides and a copper-tosylnitrenoid-complex which upon reacting with sulfoxides afforded the corresponding N-tosylsulfoximines, derived from sulfoxides in fair yields.When optically active (-)-(S)-methylphenyl sulfoxide was used, the corresponding (+)-N-tosylsulfoximine was obtained together with the sulfide derived from the N-tosylsulfilimine.The stereochemical course of the conversion of (-)-(S)-sulfoxide to (+)-N-tosylsulfoximine was found to be mainly retention (76percent) with partial racemization due to thermal pyramidal inversion of the starting sulfoxide.

A CONVENIENT PREPARATION OF N-(ARENESULFONYL)SULFOXIMINES BY OXIDATION OF N-(ARENESULFONYL)SULFILIMINES WITH SODIUM HYPOCHLORITE IN A TWO PHASE SYSTEM

N-(Arenesulfonyl)sulfilimines can be oxidized to the corresponding sulfoximines in high yields with sodium hypochlorite in an AcOEt-H2O two phase system in the presence of quaternary ammonium salts as catalysts.