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

Participants

Reaction Steps

To benzophenone hydrazone (19.6 g, 0.1 mole) contained in dimethylformamide (100 ml) together with iodine (4 ml, 1% w/v dichloromethane solution) and guanidine carbonate (75.8 g) was added peracetic acid solution (22.8 ml, 1.27 × 0.1 moles) over 60 minutes followed by a stir time of 60 minutes. The reaction mixture was poured into water (1.5 l) and washed in counter-current batch fashion with dichloromethane (200 ml and 3 × 50 ml) and water (3 × 250 ml). A UV assay at 525 nm on a suitably diluted aliquot corresponded to a yield of 60.5%.

Provenance & Evidence