Propanedinitrile, 2,2'-(1,4-cyclohexanediylidene)bis- → Tetracyanoquinodimethane

HRID 903818

Reaction equation

HRID 903818 reaction equation
[C:1]([C:3]([C:15]#[N:16])=[C:4]1[CH2:9][CH2:8][C:7](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[CH2:6][CH2:5]1)#[N:2]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:5]1[C:4](=[C:3]([C:1]#[N:2])[C:15]#[N:16])[CH:9]=[CH:8][C:7](=[C:10]([C:11]#[N:12])[C:13]#[N:14])[CH:6]=1

Participants

4

Reactant 1

HCID 73696Propanedinitrile, 2,2'-(1,4-cyclohexanediylidene)bis-

Product 1

HCID 73697Tetracyanoquinodimethane

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

According to the procedure of Fatiadi Synthesis, 1976, 133, incorporated herein by reference, the 1,4-bis(dicyanomethylene)cyclohexane is allowed to react with manganese dioxide in refluxing (110° C.) toluene for ca. 15 minutes to provide TCNQ in ca. 60% yields.

Workup

  1. customAccording to the procedure of Fatiadi Synthesis, 1976, 133

Sources & evidence

ORD record
ord-366e9c2a0e504e51b09d96e9e5139ab7
Source dataset
uspto-grants-1980_10
Patent number
US04229364

Linked notes

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