Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Selective Reduction by Lithium Bis-or Tris(dialkylamino)-aluminum Hydrides. II. Reaction of Lithium Tris(dibutylamino)-aluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups

  • Published : 1991.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

The approximate rates and stoichiometry of the reaction of excess lithium tris(dibutylamino)aluminum hydride (LT-DBA) with selected organic compounds containing representative functional groups under standardized conditions (tetrahydrofuran, $0^{\circ}C$) were studied in order to characterize the reducing characteristics of the reagent for selective reductions. The reducing ability of LTDBA was also compared with those of the parent lithium aluminum hydride and the alkoxy derivatives. The reagent appears to be much milder than the parent reagent, but stronger than lithium tri-t-butoxyaluminohydride in reducing strength. LTDBA shows a unique reducing characteristics. Thus, the reagent reduces aldehydes, ketones, esters, acid chlorides, epoxides, and amides readily. In addition to that, ${\alpha},{\beta}$-unsaturated aldehyde is reduced to ${\alpha},{\beta}$-unsaturated alcohol. Quinones are reduced to the corresponding diols without evolution of hydrogen. Tertiary amides and aromatic nitriles are converted to aldehydes with a limiting amount of LTDBA. Finally, disulfides and sulfoxides are readily reduced to thiols and sulfides, respectively, without hydrogen evolution.

Keywords

References

  1. The series Ⅰ; Submitted for publication
  2. J. Am. Chem. Soc. v.80 H. C. Brown;R. F. McFarlin
  3. J. Am. Chem. Soc. v.80 H. C. Brown;B. C. Subba Rao
  4. J. Am. Chem. Soc. v.81 H. C. Brown;A. Tsukamoto
  5. Tetrahedron Lett. v.9 H. C. Brown;C. J. Shoaf;C. P. Garg
  6. Israel J. Chem. v.1 H. C. Brown;P. M. Weissman
  7. J. Am. Chem. Soc. v.86 H. C. Brown;C. J. Shoaf
  8. J. Am. Chem. Soc. v.86 H. C. Brown;C. J. Garg
  9. J. Am. Chem. Soc. v.86 H. C. Brown;A. Tsukamoto
  10. J. Org. Chem. v.31 P. M. Weissman;H. C. Brown
  11. J. Am. Chem. Soc. v.87 H. C. Brown;P. M. Weissman
  12. J. Am. Chem. Soc. v.87 H. C. Brown;H. R. Deck
  13. Gazz. Chim. Ital. v.90 P. Longi;G. Mazzanti;F. Bernardini
  14. Inorg. Chem. v.10 R. G. Beach;E. C. Ashby
  15. Izv. Akad. Nauk SSSR, Ser. Kim. V. V. Gavrilenko;M. I. Vinnikova;V. A. Antonovich;L. I. Zakharkin
  16. Organic Syntheses via Boranes H. C. Brown;G. W. Kramer;M. M. Midland
  17. J. Am. Chem. Soc. v.88 H. C. Brown;P. M. Weissman;N. M. Yoon
  18. Synthesis J. Malek;M. Cerny
  19. J. Org. Chem. v.36 E. C. Ashby;John P. Sevenair;Frank R. Dobbs

Cited by

  1. Reaction of Sodium Cyanoaluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups vol.29, pp.12, 1991, https://doi.org/10.5012/bkcs.2008.29.12.2379
  2. Reaction of Lithium Cyanoaluminum Hydride with Selected Organic Compounds Containing Representative Functional Groups. Comparison of Reducing Characteristics between Lithium and Sodium Cyanoaluminum H vol.30, pp.7, 1991, https://doi.org/10.5012/bkcs.2009.30.7.1588
  3. Reaction of lithium tris(tert-butylthiolato)hydridoaluminate with selected organic compounds containing representative functional groups vol.65, pp.1, 2009, https://doi.org/10.1007/s10847-009-9628-4
  4. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1991, https://doi.org/10.5012/bkcs.2011.32.6.1808