136557-91-0Relevant academic research and scientific papers
Preparation of 1-Nitro-2,5-alkanediones by C-Acylation of Nitroalkanes With Enollactones
Jaeger, Volker,Seidel, Bernhard,Guntrum, Eberhard
, p. 629 - 632 (2007/10/02)
Dihydro-5-methylenefuran-2(3H)-one (4-Penten-4-olide, 1 a) and its methyl derivatives 1 b-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-.
