Nucleophilic addition of hydroxylamine, methoxylamine, and hydrazine to malononitrileoxime

被引:40
作者
Arulsamy, N [1 ]
Bohle, DS [1 ]
机构
[1] Univ Wyoming, Dept Chem, Laramie, WY 82071 USA
关键词
D O I
10.1021/jo991614t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 . H2O), and 3,5-diaminopyrazolone-4-oxime.monohydrochloride monohydrate (6 . HCl . H2O), 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).
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页码:1139 / 1143
页数:5
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