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

Participants

Reaction Steps

A solution of 0.59 g (3 mmol) of benzophenone hydrazone in 12 ml of ether is added dropwise at room temperature to a suspension of 2.95 g of nickel peroxide hydrate in 12 ml of ether, the mixture is stirred for one hour and the violet solution is filtered with suction through Celite and concentrated. The 3 mmol of diphenyldiazomethane obtained in this way are dissolved in 32 ml of absolute acetone and, while cooling in ice, added dropwise to a solution of 1.31 g (2.5 mmol) of 2-[N-(1S -menthyloxycarbonyl-3-phenylpropyl)-S-alanyl]-(1S,3S,5S)2-azabicyclo[3.3.0]octane-3-carboxylic acid (see Example 45) in 32 ml of absolute acetone. The mixture is then stirred at room temperature for 38 hours and concentrated, and the crude product is purified by column chromatography on silica gel (mobile phase toluene/ethanol 99.5:0.5 and cyclohexane/ethyl acetate 8:2).

Provenance & Evidence