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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 8
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Original Articles

Preparative Scale Stereoselective Synthesis of Methyl 4-Methyl-(Z)-2, 4-Pentadienoate

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Pages 783-790 | Published online: 05 Dec 2006

References

  • University of Kansas
  • RWTH-Aachen
  • Still , W. C. and Gennari , C. 1983 . Tetrahedron Lett. , : 4405
  • Kover , W. B. and de Souza , N. A. 1980 . J. Org. Chem. , 45 : 4226
  • Sundberg , Sundberg , R. J. , Bukowick , P. A. Holcombe , F. O. 1967 . J. Org. Chem. , 32 : 2938 Following the procedure of
  • Engler , T. A. and Falter , W. 1986 . Tetrahedron Lett. , : 4115 4119
  • Rappe , C. 1973 . Org. Synth. , 53 : 123 For related rearrangments of α,α'-dihaloketnoes, see and references cited therein
  • Notably, the dimers all have a (E)-α,β-unsaturated ester which indicates isomerization of the α,β-double bond in 1 at some stage of the process from 1 to 6, 7 and 8
  • Fractional distillation of the reaction mixture was successful on a smaller scale (50 mmol) and 1 was collected at 78–83°C/35 mm along with 5 at 53–57°C/6 mm
  • West Germany : Meckenheim . Available from Fischer Labor-und Verfahrenstechink GmbH, Industriepark Kottenforst, D-5309
  • Dauben , W. G. and Baker , W. R. 1982 . Tetrahedron Lett. , : 2611 The enhanced ratio of 1 to 2 found after distillation as compared to the ratio in the crude reaction mixture, may reflect preferential dimerization of 2 relative to 1 to Diels-Alder adducts; see
  • Bohlmann , F. and Zdero , C. 1973 . Chem. Ber. , 106 : 3779 From Wittig or Wadsworth-Emmons-Horner reactions: Stotter, P. L. and Eppner, J. B. Tetrahedron Lett. 1973, 2417; Kelly, T. R., Goerner, R. N., JR., Gillard, J. W. and Prazak, B. K. Tetrahedron Lett. 1976, 3869
  • Corey , E. J. , Kim , C. U. , Chen , R. H. K. and Takeda , M. 1972 . J. Am. Chem. Soc. , 94 : 4395 From organocopper chemistry:

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