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

Participants

Reaction Steps

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%.

Provenance & Evidence