Reaction of Hydrazoic Acid with Nitroso Compounds

Reaction of Hydrazoic Acid with Nitroso Compounds 

The synthesis of aryl azides in high yields and under mild conditions by the reaction of aromatic nitroso compounds with hydrazoic acid has been reported by Maffei and co-workers . Their results are summarized in Table 14. No intermediates have yet been isolated from this reaction, although Maffei suggested the intervention of a diazohydroxide. If the quantity of hydrazoic acid employed is less 

When hydrazoic acid labelled on the two terminal nitrogen atoms, 

The reaction has been extended by Maffei and co-workers to include the synthesis of the a-nitroazidoalkenes (265) and (266) from the corresponding pseudonitroles. Similarly the a-chloroazido-alkanes (267) and (268) have been isolated. 

Ar in ArNO % of product from linear pentazene % of product from cyclic pentazene 

---

C. Reaction of Hydrazoic Acid with Nitroso Compounds... 

---