Detrifluoroacetylation of 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-ones as a convenient synthetic strategy for acyl cyanides

• Features of fluorinated 1,3-diketones nitrozation were studied.
• Hydrates of 1,1,1-trifluoro-3-(hydroxyimino)butan-2,4-diones were isolated.
• Novel acyl nitriles synthesis was elaborated.
• Detrifluoroacetylation of 1,3-diketone derivatives proceeds under acidic conditions.

A reaction reinvestigation of fluorinated 1,3-dicarbonyl compounds with NaNO2 in acidic conditions revealed the formation of corresponding 1,1,1-trifluoro-3-hydroxyimino-butan-2,4-diones which predominantly isolated as hydrates. A novel synthesis of ethoxy-, alkyl-, (het)aryl substituted carbonylcyanides via acid-catalyzed detrifluoroacetylation of obtained 2-hydroxyimino derivatives of 1,3-dicarbonyl compounds was described.

A convenient cyanide-free synthesis of acyl cyanides was elaborated by detrifluoroacetylation of novel 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-onesFigure optionsDownload as PowerPoint slide