Oxidative hydrolysis, of nitronate salts

The oxidative hydrolysis of nitronate salts derived from primary nitroalkanes (Expt 5.84). 

THE OXIDATIVE HYDROLYSIS OF NITRONATE SALTS DERIVED FROM PRIMARY NITROALKANES... 

In an interesting sequence of reactions, Grundmann and co-workers have prepared 5-amino-4-nitroisoxazole (67) from the sodium salt of nitromalonaldehyde and hydroxylamine.59 The initially formed sodium malon-dialdoxime nitronate 65 is diacetylated and cyclized to the furazan oxide 66 acid hydrolysis, followed by rearrangement in alkali gives the 5-amino-4-nitroisoxazole (Scheme 13). The same product has also been detected in the decomposition of mercuric fulminate. 

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