81650-42-2

Upstream product

• 32894-70-5 allyl 4-nitrophenyl sulfide 
• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 107-18-6 allyl alcohol 
• 28525-01-1 Allyl 4-nitrobenzenesulfenate 
• 1849-36-1 para-nitrobenzenethiol 
• 26760-22-5 methyl p-nitrobenzenesulphinate 

Downstream Products

• 32894-70-5 allyl 4-nitrophenyl sulfide 
• 81650-46-6 1-Allyldisulfanyl-4-nitro-benzene 
• 78012-61-0 (E)-1-phenyl-4-(p-nitrophenylsulfinyl)but-3-en-1-ol 
• 78020-99-2 2,4-diphenyl-6-(p-nitrophenylsulfinylmethyl)-1,3-dioxan 
• 3729-43-9 Allyl 4-nitrophenyl sulfone 

Relevant academic research and scientific papers

Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions

A facile synthetic method for the preparation of allyl sulfoxides byS-allylation of sulfinate esters proceeds through sulfonium intermediates without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates,S-alkynylation andS-arylation were also accomplished.

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.

Copper catalyzed oxidation of sulfides to sulfoxides with aqueous hydrogen peroxide

Copper(II) complex 1 catalyzes the oxidation of sulfides to sulfoxides with 30% H2O2 in high yields. Addition of a catalytic amount of TEMPO to the reaction mixture enhances the conversion and selectivity. Complex 1 can be recycled without loss of activity.

STRUCTURAL EFFECTS UPON COMPETITIVE DECOMPOSITION PATHWAYS OF THIOSULFOXIDE INTERMEDIATES

Mixtures of sulfides and disulfides are obtained upon reaction of boron trisulfide with a series of allyl aryl sulfoxides, with the product distributions dependent upon the structures of the intermediate thiosulfoxides.

Asymmetric Induction in the Additions of Anions of Allylic Sulfoxides to Benzaldehyde

Addition reactions of anions of aryl allyl sulfoxides to benzaldehyde proceed readily in moderate yields and afford mixtures of products resulting from α- and γ-attack on the allyl anion.The γ-products all possess the (E)-configuration around the double bond, and asymmetric induction occurs in the addition to the extent that the major/minor diastereomer ratio exceeds 2:1, generally.Electronic factors are believed to be responsible for this "remote" asymmetric induction.Mixtures of all four possible diastereomers are observed in the products from α-attack and evidence is presented which suggests that the ratios of these products are as a result of epimerization of two of the chiral centres by sigmatropic rearrangement.