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

HRID 2082938Notes

Reaction equation

HRID 2082938 reaction equation
[C:1]1([C:7](=[N:14][NH2:15])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.CN(C)C(N(C)C)=N.C(OO)(=O)C>ClCCl>[C:1]1([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+:14]=[N-:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 6585Peracetic AcidHCID 664601,1,3,3-TetramethylguanidineHCID 79304Diphenylmethylidenehydrazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To diphenyl ketone hydrazone (19.6 g, 0.1 moles) dissolved in dichloromethane (100 ml) containing iodine (4 ml, 1% w/v solution) and 1,1,3,3-tetramethylguanidine (45 ml) was added peracetic acid solution (23.5 ml, 1.30 × 0.05 moles) at 0° over 60 minutes. The mixture was stirred for an additional 15 minutes. The purple-red solution was washed with water (5 × 250 ml), dried and made up to 500 ml in a volumetric flask. A UV assay on a suitably diluted aliquot corresponded to a yield of diazoalkane of 95.6%.

Workup

  1. washThe purple-red solution was washed with water (5 × 250 ml)
  2. customdried
  3. custommade up to 500 ml in a volumetric flask
  4. additionA UV assay on a suitably diluted aliquot

Sources & evidence

ORD record
ord-f644e95853914e9a86fad131c100a3b3
Source dataset
uspto-grants-1978_04
Patent number
US04083837

Reaction notes

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