89279-68-5

Upstream product

• 89279-66-3 S-(2-chloroethyl)-S-phenyl-N-(p-tolylsulfonyl)sulfoximine 
• 20451-53-0 Phenyl vinyl sulfoxide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 50-00-0 formaldehyd 
• 42153-74-2 S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfoximide 
• 10330-22-0 S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfilimine 
• 127-65-1 chloroamine-T 
• 1338062-05-7 4-methyl-N-[(2-propoxyphenyl)-λ³-iodanylidene]benzenesulfonamide 
• 89279-67-4 S-(2-chloroethyl)-S-phenyl-N-(p-tolylsulfonyl)sulfilimine 
• 5535-49-9 2-Chloroethyl phenyl sulfide 
• 100-68-5 methyl-phenyl-thioether 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Conjugate addition of amines to vinyl sulfoximides: A general method for the synthesis of β-amino sulfoximides

The synthesis of a range of β-amino sulfoximide derivatives is described. The conjugate addition of simple amines or amino acids to N-tosyl phenyl vinyl sulfoximide was achieved in moderate to good yield (41-95%). Electron poor nucleophiles such as tosyl amide or benzyl carbamate were found to be unreactive under analogous conditions.

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

An efficient preparation of β-dimethylaminovinyl sulfone and sulfoximide, and investigation of their reactivity as dipolarophiles

A simple reaction affording (E)-1-dimethylamino-2-phenylsulfonylethylene, and S-((E)-2-(N′N′-dimethylamino)ethenyl)-5-phenyl-N-(p- tolylsulfonyl) sulfoximide in high yields is described. A reversal in regioselectivity was observed when the ss-dimethylamin

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.

A study of the functional group compatibility of sulfoximination methods

The sulfoximination of a range of sulfoxides possessing functionalised side-chains using mesitylene sulfonyl hydroxylamine or iminoiodane reagents is discussed. The use of iminoiodane reagents possessing removable protecting groups (p-nosyl and Ses) is re

Cu(I)-catalyzed sulfoximination

The reaction of PhI=NTs with sulfoxides in the presence of catalytic amounts of CuOTf afforded the corresponding N-tosylsulfoximines in high yield. The use of enantiomerically pure sulfoxides allowed stereoselective access to N-tosylsulfoximines with comp

The 1,3-dipolar cycloaddition reactions of C, N-diphenylnitrone with vinyl sulfoximines

The reactions of vinyl sulfoximines (1a-e) with C,N-diphenylnitrone (2) are highly regioselective and give only 4-sulfonimidoyl-isoxazolidine cycloadducts. These reactions proceed with modest π-facial diastereoselectivity with respect to the dipolarophile

Diels - Alder Reactions of S-Vinyl-S-Arylsulfoximines

Cyclopentadiene and the known S-p-tolyl-S-vinyl-N-phthalimidosulfoximine (1a) undergo Diels-Alder reaction to give a mixture of cycloadducts in excellent yield.The structures of the cycloadducts including stereochemistry are assigned by 1H NMR spectroscopy.The crystal and molecular structure of the major cycloadduct 5d, n = 1, G = 1,2 C6H4(CO)2N was determined unequivocally by X-ray crystallographic techniques.Treatment of this major cycloadduct with hydrazine in ethanol resulted in conversion of the sulfoximine to sulfoxide group concomitant with reduction of the carbon-carbon double bond.Use of allyl alcohol as solvent in this reaction allowed conversion to the corresponding unsaturated sulfoxide 8.The previously unknown S-p-tolyl-S-vinyl-N-(p-tolylsulfonyl)-sulfoximine (1b) is somewhat more reactive than phenyl vinyl sulfone and undergoes Diels-Alder reactions with cyclic and acyclic 1,3-dienes in 81-95percent yield.The endo selectivity of vinylsulfoximine 1b is 9:2 with cyclopentadiene and 93:7 with 1,3-cyclohexadiene.With 2-methyl-1,3-butadiene the para adduct is produced regioselectively in a ratio of 4:1.Although formation of the endo adducts from vinylsulfoximine 1b and cyclopentadiene and 1,3-cyclohexadiene is not diastereoselective, the diastereomers can be separated by HPLC.The cycloadducts from 1,3-cyclohexadiene and vinylsulfoximine 1b have been converted to bicyclooct-2-ene and bicyclooct-2-en-5-one.