Divinyl sulfoxide

Base Information

• Chemical Name: Divinyl sulfoxide
• CAS No.: 1115-15-7
• Molecular Formula: C4H6 O S
• Molecular Weight: 102.157
• Hs Code.: 2930909090
• European Community (EC) Number: 621-313-4
• UNII: 4W5026ZW8G
• DSSTox Substance ID: DTXSID50912184
• Nikkaji Number: J49.640E
• Wikidata: Q27260573
• Mol file: 1115-15-7.mol

Synonyms:Divinyl sulfoxide;VINYL SULFOXIDE;1-ethenylsulfinylethene;1115-15-7;DIVINYLSULFOXIDE;Ethene, 1,1-sulfinylbis-;HSDB 2029;TL 907;BRN 1071225;Ethene, 1,1'-sulfinylbis-;UNII-4W5026ZW8G;4W5026ZW8G;3-01-00-01869 (Beilstein Handbook Reference);(Ethenesulfinyl)ethene;SCHEMBL50670;VINYL SULFOXIDE [HSDB];DTXSID50912184;TL-907;AKOS024378704;LS-162190;Q27260573

Chemical Property of Divinyl sulfoxide

Chemical Property:

• Vapor Pressure: 0.224mmHg at 25°C
• Refractive Index: n20/D 1.514
• Boiling Point: 214.8°Cat760mmHg
• Flash Point: 83.7°C
• PSA: 36.28000
• Density: 1.083g/cm³
• LogP: 1.88780
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 102.01393598
• Heavy Atom Count: 6
• Complexity: 75.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C=CS(=O)C=C
• General Description: Divinylsulfoxide (also known as vinylsulfoxide or divinyl sulfoxide) is implicated in reactions where the geometric configuration of allylic and vinylic groups is fully retained during ligand coupling via an α-sulfurane intermediate, as demonstrated in its interactions with Grignard reagents. This retention of configuration suggests a concerted mechanism without rearrangement or dissociation, supported by stereochemical and crystallographic evidence.

Technology Process of Divinyl sulfoxide

There total 3 articles about Divinyl sulfoxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

divinyl sulfide (627-51-0) → divinyl sulfoxide (1115-15-7) + Divinyl sulfone (77-77-0)

Guidance literature:

With dihydrogen peroxide; In ethanol; hexane; water; at 20 ℃; for 0.166667h;

DOI:10.1016/S1872-2067(16)62548-2

Reference yield:

bis(2-chloroethyl)sulfoxide (5819-08-9) → divinyl sulfoxide (1115-15-7) + Divinyl sulfone (77-77-0) + 1-(2-Chloroethylsulfinyl)ethene (40709-82-8) + bis(2-chloroethyl)sulfone (471-03-4)

Guidance literature:

Prod.5:<2-Chlor-aethyl>-vinyl-sulfon;

DOI:10.1111/j.1750-3639.2000.tb00253.x

Reference yield:

vinyl magnesium bromide (1826-67-1) + benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate (499140-12-4) → divinyl sulfoxide (1115-15-7) + Ethenesulfinic acid (1R,2S)-2-benzyloxycarbonylamino-1-phenyl-propyl ester

Guidance literature:

In dichloromethane; at -78 ℃; Title compound not separated from byproducts.;

DOI:10.1021/ol027232i

upstream raw materials:

bis(2-chloroethyl)sulfoxide

vinyl magnesium bromide

benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate

divinyl sulfide

Downstream raw materials:

<3-Trimethylsilyl-propyl>-vinyl-sulfid

vinyl (2-methyl-2-propyl) sulfide

4-isopropyl-thiomorpholine 1-oxide

1,1-bis(γ-trimethylsilylpropylthio)ethane

Refernces

LIGAND COUPLING THROUGH ?-SULFURANE --- COMPLETE RETENTION OF GEOMETRIC CONFIGURATION OF ALLYLIC AND VINYLIC GROUPS IN THE REACTIONS OF ALLYLIC AND VINYLIC SULFOXIDES WITH GRIGNARD REAGENTS

10.1016/S0040-4039(00)80518-3

The research explores the geometric configuration retention in the reactions of allyl and vinyl sulfoxides with Grignard reagents through the formation of an incipient α-sulfurane intermediate. The purpose of the study was to determine whether the geometric configuration of allyl and vinyl groups is preserved during these reactions. The researchers used a variety of chemicals, including p-benzenesulfonylphenyl crotyl sulfoxide, p-benzenesulfonylphenyl α-methylallyl sulfoxide, and 2-pyridyl and p-benzenesulfonylphenyl styryl sulfoxides, along with Grignard reagents such as phenyl or methyl magnesium halides. The conclusions drawn from the study were that the geometric configuration of the allyl and vinyl groups was completely retained in the coupling products, indicating a concerted process within the α-sulfurane intermediate without any rearrangement or dissociation. This finding was supported by the results of stereochemical experiments and X-ray crystallographic analysis, which confirmed the preservation of the geometric configuration in the coupling products.

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