Anthracene → Anthracene, 9-(methylthio)-

HRID 2302121Notes

Reaction equation

HRID 2302121 reaction equation
[CH3:1][S:2]SC.[CH:5]1[C:18]2[C:9](=[CH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1>C(#N)C.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][S:2][C:17]1[C:18]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 8418Anthracene2×HCID 12232Dimethyl Disulfide3×

Product 1

HCID 11064094Anthracene, 9-(methylthio)-

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6342AcetonitrileSolvent2×

Procedure

For example, in acetonitrile, dimethyl disulfide shows an irreversible first oxidation peak at 1.05 V vs Ag/O.1M AgNO3 in acetonitrile reference electrode using the technique of cyclic voltimetry. The oxidation peak of anthracene is about 400 mV more positive than that for dimethyl disulfide. Consequently, pursuant to this invention, dimethyl disulfide can be selectively oxidized electrolytically in the presence of anthracene to produce the organothiated product, 9-methylthioanthracene, in very good yield.

Sources & evidence

ORD record
ord-2cdd16daf9a14b7e92717ca99d808735
Source dataset
uspto-grants-2002_08
Patent number
US06432294B1

Reaction notes

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