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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 3
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Original Articles

Stable Difluoromethylene Olefination Solutions

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Pages 197-200 | Received 03 Apr 1973, Published online: 06 Dec 2006

References

  • Department of Chemistry, University of Minnesota, Minneapolis, Minnesota
  • Young , J. A. 1967 . Fluorine Chemistry Reviews , 1 : 359
  • Fuqua , S. A. , Duncan , W. G. and Silverstein , R. M. 1964 . Tetrahedron Lett. , : 1461
  • Naae , D. G. and Burton , D. J. 1971 . J. Fluorine Chem. , 1 : 123 and references contained therein
  • Fuqua , S. A. 1965 . J. Org. Chem. , 30 : 2543 have claimed that (C4H9)3 + CF2ClCO2Na will give modest yields of olefins from non-activated ketones. In our hands, this method has never given greater than 5–10% yields, and with activated ketones an entirely different type of reaction occurs; D. J. Burton et. al., J. Amer. Chem. Soc., 88, 5042 (1966)
  • The yield was 75% olefin after 50 hours; 70% after 143 hours; 71% after 168 hours; and 68% after 311 hours
  • 1966 . Organic Synthesis , 46 : 42 CF2Br2, CF2Cl2, (C6H5)3P, and [(CH3)2N)]3Pare all available commercially. Also, the tris-dimethylamino-phosphine can be easily prepared on a large scale, cf.

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