80351-59-3

Upstream product

• 75-71-8 Dichlorodifluoromethane 
• 3111-52-2 potassium thiophenolate 
• 78031-08-0 [(bromodifluoromethyl)sulfanyl]benzene 
• 1184-76-5 difluorodiiodomethane 
• 108-98-5 thiophenol 
• 1535-65-5 difluoromethyl phenyl sulfone 
• 882-33-7 diphenyldisulfane 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 24850-33-7 allyltributylstanane 
• 762-72-1 allyl-trimethyl-silane 
• 930-69-8 sodium thiophenolate 
• 536975-49-2 phenyl (trimethylsilyl)difluoromethyl sulfide 
• 353-59-3 halon-1211 
• 58201-66-4 (bromodifluormethyl)triphenylphosphonium bromide 

Relevant academic research and scientific papers

One-pot preparation of (RSe)2CF2 and (RS)2CF2 compounds via insertion of TMSCF3-derived difluorocarbene into diselenides and disulfides

A method for the first direct insertion of difluorcarbene, generated from TMSCF3, into diselenides and disulfides is disclosed, producing novel difluoromethyl diselenoacetals and difluoromethyl dithioacetals. The reaction conditions tolerate a range of synthetically useful and biologically relevant functional groups. The process is scalable, with two representative compounds prepared at a gram-scale in good yields, and it utilizes cheap and available reagents.

Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations

Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2+).

Fluoride-induced nucleophilic (phenylthio)difluoromethylation of carbonyl compounds with [difluoro(phenylthio)methyl]trimethylsilane (TMS-CF 2SPh)

A fluoride-induced nucleophilic (phenylthio)difluoromethylation method using TMS-CF2SPh has been achieved. This new methodology efficiently transfers "PhSCF2" group into both enolizable and non-enolizable aldehydes and ketones to giv

Difluoromethyl Phenyl Sulfone as a Selective Difluoromethylene Dianion Equivalent: One-Pot Stereoselective Synthesis of anti-2,2-Difluoropropane-1,3-diols

Intramolecular charge-charge repulsion rather than traditional steric control is responsible for the high diastereoselectivity (up to 94% de) obtained in tBuOK-induced difluoromethylenation of aldehydes 1 with difluoromethyl phenyl sulfone (2) to give symmetrical and unsymmetrical anti-2,2-difluoropropane-1,3-diols 3.

The reactions of difluorodiiodomethane with nucleophiles

Treatment of difluorodiiodomethane with phenoxides (ArO-) in DMF at room temperature gives ArOCF2I in 7-15%, the carbonates (ArOCO2Ar) being the major products, while with thiophenoxides affords difluoromethylene derivativ

Chemistry of Halogenoperfluoroalkanes> Synthesis of Fluorinated Ethers and Thioethers via Radical or Anionic Intermediates

Condensation of bromotrifluoromethane with potassium thiophenoxides in DMF is performed under pressure (2-3 atm) in a glass apparatus.Inhibition by nitrobenzene shows that a SRN1 mechanism is involved in the formation of aryl trifluoromethyl sulfides.Dichlorodifluoromethane itself reacts through a similar process to give aryl chlorodifluoromethyl sulfides.Condensation of 1,1,2-trichlorotrifluoroethane with potassium thiophenoxide or phenoxide occurs even in the presence of nitrobenzene.The formation of aryl 2,2-dichloro-1,1,2-trifluoroethyl sulfides or ethers can be explained by a chain carbanionic mechanism.

SRN1 Substitutions of Halogenoperfluoroalkanes (CF3Br or CF2Cl2) under Pressure

Radical chain fluoroalkylation of arenethiolates by CF3Br or CF2Cl2, performed under slight pressure in a glass apparatus, gives aryl polyfluoromethyl sulphides.

Reactivity of the Perhaloalkanes CF2X2 (X = Cl, Br) with Nucleophiles. 6. Coexistence of Carbene and Radical Processes Initiated by Single-Electron Transfer

In the condensation of sodium thiophenoxide with CF2BrCl in DMF at -40 deg C, two mechanisms are involved simultaneously.A carbene chain process is postulated for the formation of C6H5SCF2Br and C6H5SCF2H.A radical chain process is implicated for the formation of C6H5SCF2Cl and C6H5SCF2SC6H5.These competitive chain processes could occur after an initial one-electron transfer from the thiophenoxide to CF2BrCl, giving a caged intimate radical/anion radical pair (RARP).

SYNTHESIS OF BROMODIFLUOROMETHYL PHENYL SULFIDE, SULFOXIDE AND SULFONE

Sodium thiophenoxide reacts with dibromodifluoromethane to give bromodifluoromethyl phenyl sulfide.Peracid oxidation of the sulfide gives the corresponding sulfoxide and sulfone.The formation of the sulfide is suggested to proceed via attack of thiophenoxide on halogen to produce difluorocarbene.Capture of carbene by thiophenoxide followed by a second positive halogen abstraction reaction yields the sulfide, PhSCF2Br.The use of excess sodium thiophenoxide yields difluorobis(thiophenyl)methane, (PhS)2CF2, via a similar mechanistic scheme.