Diphenyl disulfide → [(Tridecafluorohexyl)sulfanyl]benzene

HRID 1974788Notes

Reaction equation

HRID 1974788 reaction equation
[F:1][C:2](I)([F:19])[C:3]([F:18])([F:17])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8].OCS([O-])=O.[Na+].[C:27]1([S:33]SC2C=CC=CC=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O.O>[F:1][C:2]([S:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([F:19])[C:3]([F:18])([F:17])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8]

Participants

6

Reactant 3

HCID 13436Diphenyl disulfideHCID 677331,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexaneHCID 23689980Sodium Formaldehyde Sulfoxylate

Product 1

HCID 13213429[(Tridecafluorohexyl)sulfanyl]benzeneYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Perfluorohexyl iodide (4.5 g), sodium hydroxymethanesulphinate (4 g) and phenyl disulphide (2.2 g) in dimethylformamide (10 cc) and water (0.5 cc) are stirred for 12 hours. After the usual treatment, phenyl perfluorohexyl sulphide is obtained in 40% yield.

Sources & evidence

ORD record
ord-ad3d7b28c6384f92887b21eb32467a16
Source dataset
uspto-grants-1994_02
Patent number
US05283337

Reaction notes

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