Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Facile Reduction of Acid Anhydrides with Borane in the Presence of Lithium Chloride in Tetrahydrofuran

  • Published : 1986.08.20
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Abstract

Carboxylic acid anhydrides are rapidly reduced with borane-lithium chloride (1:0.1) system to give corresponding alcohols (diols in the case of cyclic anhydride) quantitatively in tetrahydrofuran at room temperature. This reagent tolerates aromatic acid ester, nitro, and halide functional groups, however competitively reduces aliphatic ester and nitrile groups.

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References

  1. J. Org. Chem. v.35 D.M. Bailey;R.E. Johnson
  2. Can. J. Chem. v.58 M.M. Kayser;P. Morand
  3. J. Org. Chem. v.49 S. Kim;K.H. Ahn
  4. J. Org. Chem. v.45 H.C. Brown;S.C. Kim;S. Krishnamurthy
  5. Heterocycles v.18 S. Krishnamurthy;W.B. Vreeland
  6. J. Am. Chem. Soc. v.69 R.F. Nystrom;W.G. Brown
  7. Tetrahydron Lett. v.23 F. Plavac;C.H. Heathcock
  8. Tetrahedron Lett. v.9 H. Nakai;Y. Arai;N. Hamanaka;M. Hayashi
  9. J. Am. Chem. Soc. v.87 H.C. Brown;P.M. Weissman
  10. J. Am. Chem. Soc. v.88 H.C. Brown;N.M. Yoon
  11. J. Am. Chem. Soc. v.92 H.C. Brown;P. Heim;N.M. Yoon
  12. J. Korean Chem. Soc. v.21 N.M. Yoon;J.S. Cha
  13. J. Korean Chem. Soc. v.22 N.M. Yoon;J.S. Cha
  14. J. Org. Chem. v.38 N.M. Yoon;C.S. Park;H.C. Brown;S. Krishnamurthy;T.P. Stocky
  15. Org. Synth. Coll. v.1 H.T. Clarke;E.J. Rahrs
  16. J. Chem. Soc. R.K. Smalley;H.J. Suschitzky
  17. J. Am. Chem. Soc. v.85 C.C. Sweeley;R. Bentley;M. Makita;W.W. Wells

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  1. SYNTHESIS OF α,ω-ALKANEDIOLS. A REVIEW vol.26, pp.6, 1986, https://doi.org/10.1080/00304949409458163