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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 13, 1983 - Issue 6
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Original Articles

γ-Keto Esters and γ-Butyrolactones From the Reaction of Dialkoxydihydrofurans With Trimethylsilyl Iodide

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Pages 509-514 | Published online: 03 Jan 2007

References

  • House , H. O. 1972 . Modern Synthetic Reactions , Menlo Park : WA Benjamin Inc. .
  • Hirai , K. , Suzuki , H. , Kashiwagi , H. , Moro-oka , Y. and Ikawa , T. Chem. Lett. , 1982 23
  • Sakurai , H. , Sasaki , K. and Hosomi , A. Tetrahedron Lett. , 1981 745
  • Schmidt , A. H. 1981 . Aldrichimica Acta , 14 : 31 For a recent review see
  • γ-Keto esters and lactones were fully characterized by spec-troscopic means and were prepared by independent methods. Spiro lactone 7 was identical to a sample prepared by photooxidation of 2-furylbutanol-27. We do not have a satisfactory explanation for the reaction of 6 with TMSI.
  • Weinberg , N. L. and Weinberg , H. R. 1968 . Chem. Rev. , 68 : 459 For a review, see
  • Feringa , B. L. and Butselaar , R. J. Tetrahedron Lett. , 1982 1941 and references cited therein
  • The selectivity of the reaction with dimethoxydihydrofurans is remarkable as the dimethoxyacetals of α,β-unsatur ated aldehydes such as acrolein and β-phenylacrolein yielded complex product mixtures in their reactions with TMSI
  • Deketallzation is the major reaction of 2,5-disubstituted 2,5-dimethoxydihydrofurans e. g. 2,5-dimethyl-2,5-dimethoxydihydrofuran gives 3-penten-2,5-dione in 82 % yield

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