23267-68-7

Upstream product

• 7719-09-7 thionyl chloride 
• 2176-98-9 tetrapropylstannane 
• 23668-80-6 diphenyl-di-n-propyltin(IV) 
• 108-24-7 acetic anhydride 
• 629-19-6 Dipropyl disulfide 
• 143505-45-7 1-propyl 2-(trimethylsilyl)ethyl sulfoxide 
• 107-03-9 1-thiopropane 

Downstream Products

• 1113-13-9 propyl propylthiosulfonate 
• 85532-05-4 Propanethiosulfonic acid S-(1-chloro-propyl) ester 
• 70565-74-1 (Z)-propanethial S-oxide 
• 32157-29-2 thiopropanal S-oxide 

Relevant academic research and scientific papers

Visible Light-Promoted Synthesis of β-Keto Sulfoximines from N-Tosyl-Protected Sulfoximidoyl Chlorides

Under visible light, N-tosyl-protected sulfoximidoyl chlorides react with aryl alkynes to give β-keto sulfoximines. The reaction is characterized by a high functional group tolerance and good yields. It can be improved by the presence of a ruthenium photo

Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions

A base-free bis-alkyl thiolation reaction of indoles with sulfinothioates under Pummerer-type conditions is described. Sulfinothioates, activated with 2,2,2-trifluoroacetic anhydride, are demonstrated to be an efficient thiolation reagent for wide applica

Regio- and Stereoselective Chloro Sulfoximidations of Terminal Aryl Alkynes Enabled by Copper Catalysis and Visible Light

By visible-light photoredox catalysis with copper complexes, sulfoximidoyl chlorides add to terminal aryl alkynes to give the corresponding (E)-β-chlorovinyl sulfoximines with exclusive regio- and stereoselectivities in high yields. Two representative pro

REAGENT FOR LACRIMATION EXAMINATION AND METHOD OF LACRIMATION EXAMINATION

A new application of the dacryogenic component of onions and analogues of the component in the medicinal field. It is a reagent for lacrimation examination which contains as an active ingredient a compound represented by the following chemical formula: wherein R represents a C1-5 alkyl chain.

Oxidative fragmentations of 2-(trimethylsilyl)ethyl sulfoxides - Routes to alkane-, arene-, and highly substituted 1-alkenesulfinyl chlorides

The preparation of a collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl)ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl)ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl)ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis. The method is suitable for most alkane- and arenesulfinyl chlorides (3), but is limited to highly substituted vinylic sulfinyl chlorides. 1-Alkenyl 2-(trimethylsilyl)ethyl sulfoxides with reduced double bond substitution (6, 7, 11) succumb to reactions involving chlorination of the double bond. The β-effect of silicon is invoked to explain the ability of the 2-(trimethylsilyl)ethyl group to induce C-S bond scission under the oxidative cleavage reaction conditions. A mechanism is offered to account for the role played by the β-silicon atom of the 2-(trimethylsilyl)ethyl group. Indeed, the silicon atom is self-sacrificial in that it diverts the course of the reaction from the usual α-carbon chlorination mode to one of oxidative cleavage, whereby the 2-(trimethylsilyl)ethyl group is lost. The overall reaction calls upon the ability of silicon atoms to donate electron density by hyperconjugation.

Allium chemistry: Microwave spectroscopic identification, mechanism of formation, synthesis, and reactions of (E,Z)-propanethial S-oxide, the lachrymatory factor of the onion (Allium cepa)

Flow pyrolysis of 2-methyl-2-propyl 1'-propenyl sulfoxide (9b) affords a 98:2 mixture of (Z)- and (E)-propanethial S-oxide ((Z)- and (E)-5b), both characterized by Fourier transform microwave (FT-MW) spectroscopy. Sulfines (Z)- and (E)-5b are also identified by FT-MW in chopped onion volatiles and by NMR spectroscopy in onion extracts. Similarly, flow pyrolysis of 2-methyl-2-propyl vinyl sulfoxide (9c) affords (Z)- and (E)-isomers of ethanethial S-oxide (5a), identified by FT-MW methods. Pyrolysis in the presence of D2O affords (Z)-5a-d1 and (Z)-5a-d2 from 9c and (Z)-5b-d1 from 9b; (Z)-5b-d1 is also produced when an onion is homogenized in D2O. Pyrolysis of 9c with ethyl propiolate gives ethyl (E)-3-(vinylsulfinyl)acrylate (10). Neat 5a at 100°C gives acetaldehyde. On standing, 5b dimerizes to trans-3,4-diethyl-1,2-dithietane 1,1-dioxide (12a); Me3SiCH=S+-O- (5f) undergoes an analogous dimerization. Compound 5b shows moderate potency as an anticarcinogen in inducing the enzyme quinone reductase.

Sulfinyl chlorides through the oxidative chlorination of sulfenyl derivatives with trimethylsilyl acetate/sulfuryl chloride system

A new and useful procedure for the synthesis of sulfinyl chlorides is described involving a combined action of trimethylsilyl acetate and sulfuryl chloride as a oxidative chlorination system on sulfenyl derivatives.

The reaction of 2-trimethylsilylethyl sulfoxides with sulfuryl chloride. A fragmentation route to sulfinyl chlorides

Sulfinyl chlorides were prepared in good to excellent yields by reacting aryl or alkyl 2-trimethylsilylethyl sulfoxides with SO2Cl2.

Reactions of Thionyl Chloride with Tetraorganotin(IV) Compounds

The reactions of thionyl chloride with tetraorganotin(IV) derivatives (R4Sn where R = CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H4CH3) bring about cleavage of tin-carbon bonds to give dialkyl/aryltin(IV) and alkyl/aryl sulphinyl chlorides.The ease of cleavage observed on the basis of the reactivities of R4Sn follows the order: n-C4H9 > n-C3H7 > C2H5 > CH3 > C6H5CH2 >> C6H4CH3.This order is not the same as commonly known in literature.