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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 12, 1982 - Issue 6
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Original Articles

Wittig Reactions Initiated by Dealkylative Decarboxylation

, &
Pages 469-475 | Published online: 05 Dec 2006

References

  • Partridge , M. W. , Slorach , S. A. and Vipond , H. J. 1964 . J. Chem. Soc. , : 3670 Typical examples are the following: Friedel-Crafts reactions in AICI3NaCl eutectics; D. B. Bruce, A. J. S. Sorrie, D. H. Thomson, ibid., 2403. (1953); J. F. Norris, A. J. Klemka, J. Amer. Chem. Soc., 62, 1432. (1940): Hofmann eliminations in tetra-alkylammonium hydroxide melts: A. C. Cope, E. A. Trumbell, Org. Reac., 11, 317. (1960): Dealkylations in molten pyridinium hydrochloride: V. Prey, Chem. Ber., 74, 1219. (1941); J. C. Sheehan, W. F. Erman, P. A. Cruickshank, J. Amer. Chem. Soc., 79, 147. (1957)
  • Gordon , J. E. 1969 . “Techniques and Methods in Organic and Organo-metallic Chemistry,” , Edited by: Denney , D. B. 51 – 188 . New York : M. Dekker .
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  • House , H. O. 1972 . “Modern Synthetic Reactions”, , Second Edition , 682 – 709 . Meulo Park, Ca. : W. A. Benjamin .
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  • Satisfactory analytical data were obtained for all products depicted
  • The actual composition of precipitated salt I, which has a reproducible decomposition point, was ascertained by combustion analysis. Because the amount of LiCl present would depend on its relative solubility in THF, we would not expect exact stoichiometry. Nevertheless, our analyses of the crude salt suggest I is 80. mole % of the indicated phosphonium iodide and 20. mole% LiCl (Found: C, 55.09; H, 5.12/Theory: C, 55.15; H, 4.83) For our initial studies further purification of 1. was not required

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