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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 7
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Original Articles

Reaction of [3-(Dimethylamino)-2-Phenyl-Prop-2-en-1-Ylidene] Dimethylammonium Perchlorate with Grignard and Lithium Reagents

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Pages 561-570 | Published online: 05 Dec 2006

References

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  • Payne , G. and Williams , P. 1961 . J. Org. Chem. , 26 : 651
  • Southwick , P. and Kirchner , J. 1962 . J. Org. Chem. , 27 : 3305
  • The stereochemistry of the 2,3-disubstituted acroleins was assigned the E-configuration on the following basis: (1) N.M.R. shift correlation10 for the vinyl hydrogen where R = n-Bu. δE (predicted) = 6.59 δZ (predicted) = 7.30 δObserved = 6.62(2) N.M.R. shift analysis11 with Eu(fod)3 in CCl4 for the vinyl and allylic hydrogens, where R = n-Bu, indicated the vinyl hydrogen was closer than the allylic hydrogens to the carbonyl group. (3) The known E-isomer7 for the acrolein where R = Phenyl has a mp of 94°C and its semicarbazide derivative12 has a mp of 194°C. The analogous compound prepared by our method has a mp of 88–90°C and its semicarbazide derivative has a mp of 191–194°C
  • Pasto , D. and Johnson , C. 1969 . Organic Structure Determination , 174 – 175 . Englewood, NJ : Prentice-Hall .
  • Kine , K. and Sievers , R. 1977 . Aldrichimica Acta , 10 : 54 For a review see
  • Hoffman , N. , Kanakkanott , A. and Schneider , R. 1962 . J. Org. Chem. , 27 : 2687
  • Danishefsky , S. , Kitahara , T. , McKee , R. and Schuda , P. F. 1976 . J. Am. Chem. Soc. , 98 : 6715
  • Carnduff , J. 1966 . Quart. Rev. , 20 : 169 For reviews see: and S. Martin, Synthesis, 633 (1979)
  • Greenhill , J. 1977 . Chem. Soc. Rev. , 6 : 277 For a recent review of the chemistry of enaminones see
  • Infrared spectra were recorded on a Perkin-Elmer Model 457 infrared spectrophotometer, using CCl4 or CHCl3 as the solvent. NMR spectra were obtained in CCl4, CDCl3, or Me2SO-d6 solutions [(CH3)4 Si internal standard] at 60 MHz with a Varian EM-360 Spectrometer. Ultraviolet spectra were obtained with a Perkin-Elmer 552 spectrophotometer. Mass spectra were obtained on a Hitachi Perkin-Elmer RMU-6E Spectrometer. All boiling points and melting points are uncorrected and melting points were recorded on a Fisher-Johns melting-point apparatus. Gas chromatographic analysis was carried out on a Perkin-Elmer Model 900 gas chromatograph

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