Sodium nitrite (NaNO2)

Abstract

(A) tert-Butylcarbazate reacts with NaNO2 in an aqueous media to afford tert-butyl azidoformate which is a convenient reagent for the acylation of amine, hydrazine and similar compounds. (Diagram Presented) (B) N-Nitroso derivatives of secondary amines are prepared by the action of NaNO2 in aqueous acetic acid. The latter can be reduced by LiAlH4 to give the corresponding hydrazine derivatives. (Diagram Presented) (C) Oximes can also be easily obtained from malonates or malononitrile and NaNO2 under very mild conditions. Reduction of the oxime allows the formation of the amino derivative. (Diagram Presented) (D) The benzotriazole ring system is built from monoacyl-o-phenylene diamine and NaNO2 in aqueous acetic acid. (Diagram Presented) (E) NaNO2 is a very useful reagent for the production of simple aliphatic nitro compounds. An example from α,β-enones is shown here. (Diagram Presented) (F) Lindén et al. have used NaNO2 in the formation of a tricyclic alloxazines. Nitrite was the key reagent for this ring-closure step. (Diagram Presented) (G) Liu et al. have shown the utility of NaNO2 as a cocatalyst for the oxidation by TEMPO of alcohols to ketones in water. (Diagram Presented) (H) Abidi converted the isopropylidene group in geraniol chain into an alkyne group by the action of an excess of NaNO, in acetic acid. (Diagram Presented) (I) Panzella et al. showed that NaNO2 in acetate buffer (0.05) M mediated the decarboxylative conjugation of caffeic acid with glutathione under mildly acidic conditions. (Diagram Presented) © Georg Thieme Verlag Stuttgart.