Carboxylic Compounds, Nitriles, and Their Interconversion

Bruckner R (author), Hanuata M (editor) In Organic Mechanisms - Reactions, Stereochemistry and Synthesis Chapter DOI 10.1007/978-3-642-03651-4 7, Springer-Verlag Berlin Heidelberg 2010 

As you may have suspected, the correlation between nitriles and carboxylic acid derivatives suggests that the chemistry of the former should be taught from this perspective. We will pursue this approach in this chapter. 

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Furazan- and furoxan-carboxylic acids are thermally and hydrolytically unstable decomposing to a-(hydroxyimino)nitriles, but their amide, ester, halide, and nitrile derivatives are readily accessible and all undergo the expected functional group interconversions. Dicyanofuroxan reacts with hydroxylamine to give the fused oxazino compound (63) and the pyridazino analogue (64) is similarly formed with hydrazine <82H(19)1063>. 

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