Mild Oxidative Conversion of Nitroalkanes into Carbonyl Compounds in Ionic Liquids

REFERENCES

• Ballini , R. ; Petrini , M. Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) . Tetrahedron 2004 , 60 , 1017 – 1047 .
   Web of Science ®Google Scholar
• Steliou , K. ; Poupart , M.-A. Synthesis of aldehydes and ketones from nitro paraffins . J. Org. Chem. 1985 , 50 , 4971 – 4973 .
   Web of Science ®Google Scholar
• Adam , W. ; Makosza , M. ; Saha-Möller , C. R. ; Zhao , C.-G. A mild and efficient Nef reaction for the conversion of nitro to carbonyl group by dimethyldioxirane (DMD) oxidation of nitronate anions . Synlett 1998 , 1335 .
   Google Scholar
• Ceccherelli , P. ; Curini , M. ; Epifano , F. ; Marcotullio , M. C. ; Rosati , O. Oxone promoted Nef reaction: Simple conversion of nitro group into carbonyl . Synth. Commun. 1998 , 28 , 3057 – 3064 .
   Web of Science ®Google Scholar
• Shahi , P. ; Vankar , Y. D. Nef reaction of benzylic and secondary nitro compounds using bis(trimethylsilyl)peroxide . Synth. Commun. 1999 , 29 , 4321 – 4325 .
   Web of Science ®Google Scholar
• Narayana , C. ; Reddy , N. K.; Kabalka G. W. Sodium percarbonate: A mild reagent for conversion of tosylhydrazones and nitroalkanes to carbonyl compounds . Synth. Commun. 1992 , 22 , 2587 – 2592 .
   Web of Science ®Google Scholar
• Olah , G. A. ; Arvanaghi , M. ; Vankar , Y. D. ; Prakash , G. K. S. Improved transformation of nitro compounds into carbonyl compounds by hydrogen peroxide/potassium carbonate . Synthesis 1980 , 662 – 665 .
   Google Scholar
• McMurry , J. E. ; Melton , J. ; Padgett , H. A new method for converting nitro compounds into carbonyls: Ozonolysis of nitronates J . Org. Chem. 1974 , 39 , 259 – 260 .
   Google Scholar
• Williams , J. R. ; Unger , L. R. ; Moore , R. H. Reaction of singlet oxygen with nitronate salts: Conversion of nitro compounds into carbonyls . J. Org. Chem. 1978 , 43 , 1271 – 1272 .
   Google Scholar
• Tokunaga , Y. ; Ihara , M. ; Fukumoto , K. A mild oxidative transformation of nitro compounds into ketones by tetrapropylammonium perruthenate . J. Chem. Soc. Perkin Trans. 1997 , 1 , 207 – 210 .
   Google Scholar
• Bortolini , O. ; De Nino , A. ; Fogagnolo , M. ; Fantin , G. ; Maiuolo , L. ; Tocci , A. Oxidative cleavage of nitroalkenes with hydrogen peroxide in environmentally acceptable solvents . Chem. Lett. 2007 , 36 , 472 – 473 .
   Web of Science ®Google Scholar
• McKillop , A. ; Sanderson , W. R. Sodium perborate and sodium percarbonate: Cheap, safe, and versatile oxidising agents for organic synthesis . Tetrahedron 1995 , 51 , 6145 – 6166 .
   Web of Science ®Google Scholar
• Muzart , J. Sodium perborate and sodium percarbonate in organic synthesis . Synthesis 1995 , 1325 – 1347 .
   Google Scholar
• Sandefur , L. O. Catalyst for oxidative Nef reaction using basic hydrogen peroxide . Patent WO 98/55437, 1998.
   Google Scholar
• Ono , N. The Nitro Group in Organic Synthesis ; Wiley : New York , 2001 .
   Google Scholar
• For the synthesis of bmim(OTf) see Bonhote , P. ; Dias , A.-P. ; Papageorgiou , N. ; Kalyanasundaram , K. ; Gratzel , M. Hydrophobic, highly conductive ambient-temperature molten salts . Inorg. Chem. 1996 , 35 , 1168 .
   PubMed Web of Science ®Google Scholar
• Seddon , K. R. ; Stark , A.; Torres M.-J. Influence of chloride, water, and organic solvents on the physical properties of ionic liquids . Pure Appl. Chem. 2000 , 72 , 2275 – 2287 .
   Web of Science ®Google Scholar
• Wasserscheid , P. ; Welton , T. Ionic Liquids in Synthesis ; Wiley-VCH : Weinheim , 2003 .
   Google Scholar
• Huddleston , J. G. ; Willauer , H. D. ; Swatloski , R. P. ; Visser , A. E. ; Rogers , R. D. Room-temperature ionic liquids as novel media for “clean” liquid–liquid extraction . Chem. Commun. 1998 , 1765 – 1766 .
   Web of Science ®Google Scholar