20867-84-9Relevant academic research and scientific papers
Ketones as electrophile in nitroaldol reaction: Synthesis of β,β-disubstituted-1,3-dinitroalkanes and allylic nitro compounds
Costa, Jeronimo S.,Gomes, Alex O.,Pereira, Vera Lúcia P.,de Souza, Douglas L. F.
, p. 1575 - 1583 (2021/07/06)
β,β-Disubstituted-1,3-dinitro compounds were obtained exclusively with an overall yield of 83% through a domino nitroaldol/elimination/1,4-addition process, when excess nitromethane was added to cyclohexanone or butanone using DBU (1,8-diazabicyclo[5.4.0]
A total synthesis of isosolanone
Lee,Jang,Chae,Park
, p. 3037 - 3046 (2007/10/02)
Nitroaldol reaction of acetone with nitromethane in the presence of base to give a nitroalcohol 3, followed by acetylation, and subsequent reduction of the resultant acetate 4 with NaBH4 gave 2-methyl-1 nitropropane 5. Michael reaction of 5 in base with acrylonitrile to give nitronitrile 6, and Nef conversion of the nitro group resulted in the corresponding ketonic nitrile 7. Wittig olefination of the ketonic nitrile with 3-methyl-2-butenyl triphenylphosphonium bromide 8 gave dienenitrile 9, which upon treatment with MeLi, followed by acidic work up, provided isosolanone 2.
