bis(methoxycarbonyl)methylidene-imino-azanium

Synthesis Reference(s)

Synthetic Communications, 17, p. 1709, 1987 DOI: 10.1080/00397918708063988
Synthesis, p. 658, 1971 DOI: 10.1055/s-1971-21790

Synthesis

The Preparative Method of Dimethyl Diazomalonate: diazomalonates are generally prepared by diazo transfer reaction of malonates and sulfonyl azides. A recent modification employs polystyrene-supported trialkylammonium azide (generated in situ) under phase-transfer catalysis conditions and allows for facile isolation.

Precautions

Dimethyl diazomalonate has been utilized more extensively than has diethyl diazomalonate due to the explosion hazard of the latter. Nonetheless, care should be taken in the preparation and handling of dimethyl diazomalonate. Storage at low temperatures is recommended. The decomposition of dimethyl diazomalonate evolves nitrogen and can result in high pressures.