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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 10, 1980 - Issue 11
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Original Articles

Symmetrical Ketones from Aldehyde Trimethylsilyl Enol Ethers on Storage: A Cautionary Note

Pages 863-866 | Published online: 06 Dec 2006

References

  • Rasmussen , J. K. 1977 . Synthesis , : 91 See and E. W. Colvin, Chem. Soc. Rev., 7, 15 (1978) for recent reviews
  • House , H. O. , Czuba , L. J. , Gall , M. and Olmstead , H. D. 1969 . J. Org. Chem. , 34 : 2324
  • These small amounts of aldehyde can also be removed by more efficient spinning band distillation. The impurities did not appear to dramatically affect our enolate reactions. All products were characterized by comparison with authentic materials using gc-mass spectrometry on an LKB 9000
  • Garst , M. E. 1979 . J. Org. Chem. , 44 : 1758 8-Pentadecanone has been reported as a major product from an octanal enolate reaction. Both 8-pentadecanone and octanal were absent in the starting silyl enol ether used in the reported reaction
  • Garst , M. E. , Bonfiglio , J. N. , Grudoski , D. A. and Marks , J. 1978 . Tetrahedron Lett. , : 2671 and J. Org. Chem., in press
  • Mukaiyama , T. 1977 . Angew. Chem. Int. Ed. , 16 : 817 Normally these aldol reactions require titanium tetrachloride
  • Scott , L. T. 1978 . Tetrahedron Lett. , : 4637 Facile Cannizarro-type reactions with amine anions as hydride sources have been reported; C. Kowalski, et al., J. Org. Chem., 43, 2601 (1978); and references cited therein

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