Diphenyl disulfide → [(Tridecafluorohexyl)sulfanyl]benzene

HRID 1090951Notes

Reaction equation

HRID 1090951 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-75b7b2c444944d239d4aa35ac0fc7bb8
Source dataset
uspto-grants-1992_01
Patent number
US05082945

Reaction notes

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