54857-11-3

Upstream product

• 16192-04-4 1-methyl-4-(2-methylallylsulfonyl)benzene 
• 74-88-4 methyl iodide 
• 513-35-9 2-methyl-but-2-ene 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 119305-98-5 (E)-2-methyl-2-butenyl p-toluenesulfinate 
• 16192-08-8 p-tolylsulfonylallene 
• 917-54-4 methyllithium 
• 1950-78-3 p-toluenesulfonyl iodide 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 16192-07-7 4-tosylacetonitrile 
• 7257-26-3 sodium p-toluenesulfinate tetrahydrate 

Downstream Products

• 344312-86-3 2-methyl-2-<1-(p-tolylsulphonyl)ethyl>oxiran 
• 99285-75-3 2,3-dimethyl-3-p-tolylsulphonylocta-1,7-diene 
• 120780-80-5 1-methyl-1-propen-2-yl-2-p-tolylsulphonylmethylcyclopentane 

Relevant academic research and scientific papers

Palladium-Catalyzed Allylic Sulfinate-Sulfone Rearrangements

Upon treatment with a zero-valent palladium catalyst, tetrakis(triphenylphosphine)palladium, in tetrahydrofuran under mild conditions allylic p-toluenesulfinates underwent α- or γ-rearrangements of the sulfonyl group via ionic intermediates to give allylic sulfones.The regiochemistry of the rearrangements depends on the character of the intermediary allylic cationic carbons generated and the steric hindrance involved therein.Keywords - allylic sulfinate; allylic sulfone; palladium catalyst; sulfinate-sulfone rearrangement; regiochemistry; tetrakis(triphenylphosphine)palladium.

Convenient Methods for the Preparation of Vinylic and Allylic Sulfones from Alkenes, Haloalkanes, and Aldehydes. Stereochemistry of the Conversion of Vinylic Sulfones to the Corresponding Allylic Sulfones

1- or 2-p-Tolylsulfonyl(=tosyl)-1-alkenes, vinylic sulfones, were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration and also from 1-haloalkanes by the homologation or unhomologation methods.The vinylic sulfones thus prepared were further converted to the corresponding allylic sulfones under basic conditions.The stereochemistry of this conversion was discussed.One-carbon homologated allylic sulfones were directly obtained from aldehydes in good yields by the reaction with diethyl phenylsulfonylmethylphosphonate and 1,8-diazabicycloundec-7-ene (DBU) under mild conditions.

CONVENIENT METHODS FOR THE PREPARATION OF VINYLIC AND ALLYLIC SULFONES FROM ALKENES

1 or 2-p-Toluenesulfonyl(=tosyl)-1-alkenes were regioselectively prepared from 1-alkenes via iodosulfonization or sulfonylmercuration, respectively.Conversion of 1-tosyl-1-alkenes to the corresponding allylic sulfones, 1-tosyl-2-alkenes, was achieved by t

HOMOLYTIC DISPLACEMENT AT CARBON. X. TOLUENESULPHONYL IODIDE AS A SOURCE OF TOLUENESULPHONYL RADICALS FOR THE FORMATION OF ALLYL-, BENZYL-, CYCLOPROPYLCARBINYL-, SPIROCYCLOPROPYLCYCLOALKYL-, BICYCLOALKYL-, AND BICYCLOALKYL-4-TOLYLSULPHONES FROM ORGANOCOBALOXIMES

4-Toluenesulphonyl iodide reacts thermally at alkylsulphone.Spiro- and bicyclo-alkyl compounds are also formed with other free radical precursors.The reactions are believed to take place through a chain mechanism in which cobaloxime(II), present adventitiously or formed by partial homolysis of the substrate, abstracts iodine from the toluenesulphonyl iodide to give the toluenesulphonyl radical, which attacks the organic ligand of the cobaloxime, preferably at the terminal olefinic carbon, thereby displacing cobaloxime(II) and giving the observed organic product.

A 1,3-Rearrangement of Allylic Sulphones Caused by m-Chloroperbenzoic Acid and Sodium Hydrogen Carbonate

The reaction of allylic sulphones with m-chloroperbenzoic acid in the presence of aqueous sodium hydrogen carbonate can result in 1,3-allylic rearrangement or isomerisation of the double bond depending on the structure of the allylic sulphone.Subsequent e