Phosgene Oxime - Preparation and Reactions

Preparation and Reactions

Phosgene oxime can be prepared by reduction of chloropicrin:

Cl3CNO2 + 2 Sn + 5 HCl + H2O → Cl2C=N-OH + 2 H3O

The observation of a transient violet color in the reaction suggests intermediate formation of trichloronitrosomethane (Cl3CNO). Early preparations, using stannous chloride as the reductant, also started with chloropicrin

The compound is electrophilic and thus sensitive to nucleophiles, including base hydrolysis:

Cl2CNOH + 2 NaOH → CO2 + NH2OH + 2 NaCl + H2O

Similar processes provide an easy way to destroy this dangerous compound. Hydrazine converts it to HCN and N2.

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