Arulsamy, Bohle
Jan 28, 2000
Citations
0
Influential Citations
33
Citations
Journal
The Journal of organic chemistry
Abstract
The chemistry of malononitrileoxime, HONC(CN)(2), with respect to nucleophilic addition to ammonia, methylamine, hydroxylamine, methoxylamine, and hydrazine is reported. Whereas the poorly nucleophilic ammonia and methylamine do not react, hydroxylamine, methoxylamine, and hydrazine add to the nitrile groups of the oxime, yielding the corresponding amidoximes and amidrazones. Depending on the stoichiometry of the reactions, hydroxylamine and hydrazine add to one or both of the nitrile groups; methoxylamine adds to only one of the nitrile groups. Three of the products, namely, cyanoacetamidoxime (1), 3-amino-2,3-hydroxyiminopropionitrile monohydrate (2.H(2)O), and 3,5-diaminopyrazolone-4-oxime monohydrochloride monohydrate (6.HCl.H(2)O), are characterized by single-crystal X-ray diffraction data. All of the products exhibit exothermic decomposition properties with heats of decomposition in the range of 500-1500 kJ mol(-)(1).