Iodine → 1,1'-(Diazomethylene)bis(benzene)

HRID 2082942Notes

Reaction equation

HRID 2082942 reaction equation
[C:1](=[N:14][NH2:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.II.C(OO)(=O)C>CN(C)C=O>[C:2]1([C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:14]=[N-:15])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 6585Peracetic AcidHCID 79304Diphenylmethylidenehydrazine

Product 1

HCID 612301,1'-(Diazomethylene)bis(benzene)

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To benzophenone hydrazone (4.9 g, 0.025 moles) in dimethylformamide (25 ml) containing iodine (1 ml, 1% w/v solution) and excess Dowex 1 × 2 quaternary ammonium hydroxide resin saturated with dimethyl formamide was added peracetic acid solution (5.7 ml, 1.27 × 0.025 m. moles) at 15° over 60 minutes.

Sources & evidence

ORD record
ord-d65c50f7aae244e8a3fccd417373dd2c
Source dataset
uspto-grants-1978_04
Patent number
US04083837

Reaction notes

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