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Synthesis 1991; 1991(8): 629-632
DOI: 10.1055/s-1991-26530
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Herstellung von 1-Nitro-2,5-alkandionen durch C-Acylierung von Nitroalkanen mittels Enollactonen

Volker Jäger* , Bernhard Seidel, Eberhard Guntrum
  • *Institut für Organische Chemie der Universität, Am Hubland, D-8700 Würzburg, Germany
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Publication Date:
29 April 2002 (online)

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Preparation of 1-Nitro-2,5-alkanediones by C-Acylation of Nitroalkanes With Enollactones Dihydro-5-methylenefuran-2(3H)-one (4-Penten-4-olide, 1a) and its methyl derivatives 1b-d in dimethyl sulfoxide C-acylate the sodium or potassium salts of nitromethane or -ethane (2, 3) to afford the 1-nitro-2,5-alkanediones 4, 5 in good yield. Novel 2-nitro-2-cycloalken-1-ones 7 and 8 are obtained from the 3,4-dihydro-2H-pyran-2-one 6 and from 4,4-dimethyl-1-nitro-2,5-hexanedione (4d), respectively. The C/O selectivity of nitronate acylation by RCOX is qualitatively correlated with the strength (pKa) of the acid HX conjugated to the leaving group X-.