The transformations of fluoroalkyl-containing 2-arylhydrazono-1,3-dicarbonyl compounds with methylamine

详细信息    查看全文

• 作者：E.V. Shchegol’ ; kov ; Ya.V. Burgart ; V.I. Saloutin
• 刊名：Journal of Fluorine Chemistry
• 出版年：2007
• 出版时间：July 2007
• 年：2007
• 卷：128
• 期：7
• 页码：779-788
• 全文大小：783 K

文摘

Fluoroalkylated 1,2,3-triketone 2-arylhydrazones and 2-arylhydrazono-3-oxo esters react variously with methylamine depending on the structure of the fluorinated substituent. 2-Arylhydrazono-1,3-dicarbonyl compounds having “short” fluoroalkyl substituents condense with methylamine at the carbonyl group attached to the non-fluorinated substituent whereas ones containing a lengthy polyfluoroalkyl substituent undergo haloformic cleavage as a result of the amine addition at the carbonyl group bearing such a substituent. The resulting 2-arylazo-3-(N-methyl)amino-1-polyfluoroket-2-en-1-ones and 1-(N-methyl)amino-2-arylhydrazono-3-fluoroalkyl-3-oxopropanamides have complexing properties, and they can bind to nickel(II) and copper(II) ions. Nickel chelates can be obtained by a three-component condensation of 2-arylhydrazono-1,3-dicarbonyl compounds and methylamine in the presence of nickel(II) cations.