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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 1
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Original Articles

The Palladium Assisted Transfer Reduction of α, β-Unsaturated Nitroalkenes Using Sodium Hypophosphite: A Synthesis of Oximes

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Pages 91-96 | Published online: 05 Dec 2006

References

  • Hudlicky , M. 1984 . Reductions in Organic Chemistry , 13 Chichester : Ellis Horwood Ltd. . For recent leading reviews see:, R. A. W. Johnstone, A. H. Wilby and I. D. Entwistle, Chem. Rev., 85, 129 (1985) and references cited therein
  • Entwistle , I. D. , Gilkerson , T. , Johnstone , R. A. W. and Telford , R. P. 1978 . Tetrahedron , 34 : 213
  • Entwistle , I. D. , Jackson , A. E. , Johnstone , R. A. W. and Telford , R. P. 1977 . J. Chem. Soc. Perkin-I , : 443
  • Sala , R. , Doria , G. and Passarotti , C. 1984 . Tetrahedron Lett. , 25 : 4565
  • Monti , D. , Gramatica , P. , Speranza , G. and Manitto , P. 1983 . Tetrahedron Lett. , 24 : 417
  • Ram , S. and Ehrenkaufer , R. E. 1984 . Tetrahedron Lett. , 25 : 3415
  • The formation of carbonyl compounds from nitroolefins has been reported using Raney nickel and sodium hypophosphite.5
  • The conversion of β-nitrostyrene under catalytic transfer reduction conditions (palladium/formic acid) to phenylacetaldehyde oxime was casually mentioned without any experimental details.3
  • Varma , R. S. and Kabalka , G. W. 1984 . Synth. Commun. , 14 : 1093 R. S. Varma and G. W. Kabalka, Synth. Commun., 15, 151 (1985)
  • Mourad , M. S. , Varma , R. S. and Kabalka , G. W. 1985 . J. Org. Chem. , 50 : 133
  • Mourad , M. S. , Varma , R. S. and Kabalka , G. W. 1984 . Synth. Commun. , 14 : 1099
  • Mourad , M. S. , Varma , R. S. and Kabalka , G. W. 1985 . Synthesis , R. S. Varma, M. Varma and G. W. Kabalka, Tetrahedron Lett., 26, 000 (1985)
  • Varma , R. S. , Varma , M. and Kabalka , G. W. 1985 . Synth. Commun. , 15
  • Varma , R. S. and Kabalka , G. W. 1985 . Heterocycles , 23 : 139
  • Varma , R. S. and Kabalka , G. W. 1985 . Chem. Lett. , : 243
  • Varma , R. S. and Kabalka , G. W. 1985 . Synth. Commun. , 15 : 443
  • At elevated temperatures (>50°), concomitant formation generation of the corresponding carbonyl compounds was observed as the common feature
  • Rylander , P. N. 1967 . Catalytic Hydrogenations over Platinum Metals , 22 181 – 186 . New York : Academic Press .
  • Gairaud , C. B. and Lappin , G. R. 1953 . J. Org. Chem. , 18 : 1
  • Using catalytic amounts (10% palladium-charcoal, by weight) reactions were incomplete even after 24 hrs. at room temperature
  • Further confirmation of the structure of the product was provided by the hydrolysis22 to phenylacetone: 1H-NMR(CDCl3) δ:7.26 (m, 5H, Ar-H), 3.69 (s, 2H, CH2) and 2.15 (s, 3H, -COCH3); 13C-NMR (CDCl3) δ:206·2 (C=0), 51·1 (CH2) and 29.3 (CH3)
  • DePuy , C. H. and Ponder , B. W. 1959 . J. Am. Chem. Soc. , 81 : 4629
  • 1969 . Standard Spectra Collection , Sadtler Research Laboratory . and 4007C (1978) 6160M

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