106708-06-9

Upstream product

• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 504-61-0 (E)-but-2-enol 
• 7204-29-7 trans-2-butenyl acetate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 536-57-2 p-toluene sulfinic acid 

Downstream Products

• 89268-70-2 (R)-1-(but-3-en-2-ylsulfonyl)-4-methylbenzene 
• 89268-66-6 (S)-(+)-1-buten-3-yl p-tolyl sulfone 
• 24931-66-6 2-butenyl p-tolyl sulfone 
• 68978-36-9 p-tolyl α methylallylsulfone 
• 68276-71-1 (2E)-1-(2-butenylsulfonyl)-4-methylbenzene 

Relevant academic research and scientific papers

Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates

The isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols access to sulfinates has been developed. Various primary, secondary, and tertiary alcohols could be compatible with the established protocols. Notably, such an isocyanide-induced synthetic strategy presented the advantages of simple operation, good functional group tolerance, and more than 40 examples up to 99% yields. (Figure presented.).

Palladium-Catalyzed Asymmetric Allylic Sulfonylation

The palladium-catalyzed asymmetric sulfonylation of allylic substrates rac-7a,b and rac-8a,b in the presence of the chiral phosphino-oxazoline ligand 3a gave the allylic sulfones 9a and 9b with ee-values of 59percent and 88percent, respectively, in high yield.In the presence of ligand ent-3b the enantiomeric allylic sulfones ent-9a and ent-9b were obtained with ee-values of 57percent and 93percent in high yield.

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.

Rearrangement of Some Allylic Sulphinate Esters to Allylic Sulphones. Ion-pair and Sigmatropic Shift Mechanisms

The mechanism of rearrangement of a number of allylic sulphinate esters to the corresponding allylic sulphones on heating in formamide has been investigated as a function of substrate structure.Simple systems such as crotyl and α-methylallyl-sulphinate ap