N-Nitrosation by Nitrite Ion in Neutral and Basic Medium

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Science  28 Sep 1973:
Vol. 181, Issue 4106, pp. 1245-1247
DOI: 10.1126/science.181.4106.1245


Formaldehyde catalyzed the conversion of various secondary amines to nitrosamines in the pH range 6.4 to 11.0. Chloral was also an effective catalyst. The reaction proceeds easily enough to have potential synthetic applications; the proposed mechanism could explain some reported anomalies regarding the synthesis of carcinogenic N-nitroso compounds in vivo and in vitro.