Science of Synthesis

Blakemore, P. R., Science of Synthesis, (2005) 21, 884.

N-Nitro and N-nitroso amides are grouped here into a single product subclass, as they exhibit comparable reactivity and are obtained by analogous synthetic methods. Their chemistry has been reviewed.[‌147‌,‌244‌] Both types of amide generally undergo nucleophilic attack at the carbonyl group and readily engage in acyl substitution reactions with a variety of nucleophiles.[‌375‌] An example of this reactivity mode, the basic hydrolysis of N-alkyl N-nitroso amides, provides a well-known synthesis of diazoalkanes through tautomerization/dehydration of the resulting N-alkyl-N-nitrosoamine nucleofuge.

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References

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• 8.Meeeee-Meee, (8888) M 8-8, 8888.
• 8.Meeeee-Meee, (8888) M 8-8, 8888.