Key influence of the nature of the substituent in the propynal molecule on the outcome of its reaction with vicinal di(N-hydroxyamine)

作者：Tretyakov E V^*; Romanenko G V; Stass D V; Mareev A V; Medvedeva A S; Ovcharenko V I

来源：Russian Chemical Bulletin, 2008, 57(3): 601-607.

• nitronyl nitroxides
• hydroxylamines
• prop-2-ynals
• alkynes
• nucleophilic addition
• organogermanium compounds

The reaction of propynals X-C C-CHO, where X-Alk or Ar, with 2,3-di(N-hydroxyamino)-2,3-dimethylbutane gives exclusively 1-X-2-(1-hydroxy-4,4,5,5-tetramethylimidazolidin-2-ylidene)ethanones. In the case of X - Me(3)Si, the reaction affords 2-(2-trimethylsilylethynyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol. The reaction of propynal containing X - Et(3)Ge yields both types of the products. The resulting imidazolidine-1,3-diol call be quantitatively isomerized to to imidazolidin-2-ylideneethanone, oxidized to 2-[2-(triethylgermyl)ethynyl]-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl, or transformed into ethynyl-substituted nitronyl nitroxide.

• 出版日期2008-3