34008-91-8

Usage

InChI:InChI=1/C5H10O2S/c1-3-5-8(6,7)4-2/h3H,1,4-5H2,2H3

Upstream product

• 5296-62-8 allyl ethyl sulfide 
• 65832-95-3 (E)-ethyl 1-propenyl sulfone 
• 69113-41-3 (Z)-ethyl 1-propenyl sulfone 
• 75-03-6 ethyl iodide 
• 682-91-7 ethyl ethanethiosulfonate 
• 16212-05-8 (allylsulfonyl)benzene 
• 2550-04-1 allyltriethoxysilane 
• 106-95-6 allyl bromide 
• 594-44-5 Ethanesulfonyl chloride 

Downstream Products

• 1448510-33-5 S-(1,7-dioxo-1,7-diphenylheptan)-4-yl O-ethyl carbonodithioate 
• 1469985-56-5 C₁₅H₁₉NO₂ 

Relevant academic research and scientific papers

SO2 conversion to sulfones: Development and mechanistic insights of a sulfonylative Hiyama cross-coupling

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.

Eosin-Mediated Alkylsulfonyl Cyanation of Olefins

Eosin-Y (EY)-mediated alkylsulfonyl cyanation of olefins was shown to afford alkylsulfonyl nitriles in good yields. On the basis of transient absorption spectroscopy, the reaction was shown to proceed via photoinduced electron transfer from 3EY? to an O-cyanated derivative of the photocatalyst, formed in situ, with generation of the corresponding sulfinate that is oxidized by EY?.+ into a sulfonyl radical. Addition of the latter on the olefin, followed by a radical cyano group transfer, then furnished the nitrile along with a RSO2 radical sustaining the radical chain.

Synthesis of allyl sulfones from potassium allyltrifluoroborates

Potassium allyltrifluoroborates underwent a bora-ene reaction with sulfur dioxide in the absence of Lewis acid catalysts to give sulfinyloxy-trifluoroborates, which subsequently undergo alkylation with electrophiles to produce sulfones in up to 91% yield. Benzyl halides and haloacetic acid derivatives can be used as the alkylation reagents while the Sanger reagent undergoes a SNAr reaction with sulfinyloxy-trifluoroborates to produce the corresponding 2,4-dinitrophenylsulfone. The developed method allows the transformation of potassium allyltrifluoroborates into allyl sulfones.

One-pot synthesis of symmetric 1,7-dicarbonyl compounds via a tandem radical addition-elimination-addition reaction

A novel approach to synthesize symmetric 1,7-dicarbonyl compounds via a tandem radical addition-elimination-addition reaction of S-carbonylmethyl xanthates with allylmethylsulfone and its analogues has been developed. Radicals were produced from S-carbonylmethyl xanthates by adding dilauroyl peroxide and reacted with allylmethylsulfone or analogues to generate terminal olefins as intermediates. The excessive radicals reacted with the intermediate olefins immediately to give adducts of symmetric 1,7-dicarbonyl compounds. This is an efficient method to synthesize 1,7-dicarbonyl compounds under mild conditions. The Royal Society of Chemistry 2013.

A convenient synthesis of sulfones using zinc mediated coupling reaction of sulfonyl chlorides with alkyl halides in aqueous media

An efficient procedure for the preparation of sulfones has been developed through a simple reaction of aromatic sulfonyl chlorides with suitable alkyl halides mediated by commercial zinc powder in aqueous media at 0 °C ~ room temperature.

A convenient method for the synthesis of β,γ-unsaturated sulfones through zinc-mediated C-S coupling reaction

Through zinc-mediated coupling reaction of allylic bromides with alkane- or arenesulfonyl chlorides, β,γ-unsaturated sulfones were obtained with moderate to good yields.

Structure-Stability Relationships in Unsaturated Sulfur Compounds. III. A Thermodynamic and 13C MNR Spectroscopic Study of the Conformations of Vinyl Sulfones

The conformations of the stable rotamers of alkyl 1-propenyl sulfones have been studied in a thermodynamic and 13C NMR spectroscopic study.The most stable rotamer of the E isomer was found to have the anticlinal conformation.The Z isomer will probably adopt a nearly anticlinal conformation.

Elimination and Addition Reactions. 36. Acceleration of Nucleophilic Eliminative Ring Fission by Bond Strain

Rates of eliminative ring fission of cyclic ethers bearing carbanion stabilizing groups have been measured with a view to assessing the contribution of ring strain to the ease of cleavage of bonds in elimination reactions. (Ethylsulfonylmethyl)oxiran (4)