Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Direct Transformation of Carboxylic Acids into Aldehydes through Acyloxy-9-borabicyclo[3.3.1]nonane$^1$

  • Published : 1988.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

New methods for the direct reduction of carboxylic acids to aldehydes through the treatments of B-acyloxy-9-borabicyclo[3.3.1]nonane (acyloxy-9-BBN) with tert-butyllithium and 9-borabicyclo[3.3.1]nonane or with lithium 9-boratabicyclo[3.3.1]nonane (Li 9-BBNH) are described. Both these systems provide the corresponding aldehydes from various carboxylic acids in high yields. A mechanism for the recuction through stepwise treatment of acyloxy-9-BBN with tert-butylithium and 9-BBN, which seems to involve the hydride migration through 9-BBN, is proposed and discussed in connection with the reduction through treatment of acyloxy-9-BBN with Li 9-BBNH.

Keywords

References

  1. A part of this work was presented at the 192nd American Chemical Society National Meeting
  2. Compendium of Organic Synthetic Methods v.1;2;3 I. T. Harrison;S. Harrison
  3. Org. Reac. v.8 E. Mosettig
  4. Ber. v.51 K. W. Rosenmund
  5. Org. Reac. v.4 E. Mosettig
  6. Recl. Trav. Chim. Pays-Bas. v.90 J. A. Peters;H. van Bekkum
  7. Recl. Trav. Chim. Pays-Bas. v.100 J. A. Peters;H. van Bekkum
  8. J. Org. Chem. v.34 J. D. Citron
  9. Chem. Commun. S. P. Dent;C. Eaborn;A. Pidcock
  10. J. Chem. Soc. H. Stephen
  11. J. Am. Chem. Soc. v.69 A. E. Finholt;A. C. Bond, Jr.;H. I. Schlesinger
  12. Tetrahedron v.35 H. C. Brown
  13. Angew. Chem. v.64 F. Weygand;G. Eberhardt
  14. J. Am. Chem. Soc. v.83 H. C. Brown;A. Tsukamoto
  15. Tetrahedron Lett. L. I. Zakharkin;I. M. Khorlina
  16. J. Org. Chem. v.31 P. M. Weissman;H. C. Brown
  17. J. Am. Chem. Soc. v.86 H. C. Brown;A. Tsukamoto
  18. J. Am. Chem. Soc. v.80 H. C. Brown;B. C. Subba Rao
  19. Tetrahedron Lett. H. C. Brown;C. J. Shoaf;C. P. Garg
  20. J. Am. Chem. Soc. v.86 H. C. Brown;C. P. Garg
  21. Bull Chem. Soc. Jpn. v.52 T. Izawa;T. Mukaiyama
  22. J. Chem. Soc., Perkin Trans v.1 I. D. Entwistle;P. Boehm;R. A. W. Johnstone;R. P. Telford
  23. Chem. Lett. M. Mukai;Mukaiyama
  24. Tetrahedron Lett. R. O. Hutchins;M. Markowitz
  25. Tetrahedron Lett. J. H. Babler;B. J. Invergo
  26. Tetrahedron Lett. L. I. Zakharkin;V. V. Gavrilenko;D. N. Maslin;I. M. Khorlina
  27. Tetrahedron Lett. T. E. Cole;R. Petit
  28. J. Am. Chem. Soc. v.106 H. C. Brown;J. S. Cha;B. Nazer;N. M. Yoon
  29. J. Org. Chem. v.52 H. C. Brown;J. S. Cha;N. M. Yoon;B. Nazer
  30. Tetrahedron Lett. v.28 J. S. Cha;J. E. Kim;S. Y. Oh;J. C. Lee;K. W. Lee
  31. J. Org. Chem. v.52 J. S. Cha;J. E. Kim;K. W. Lee
  32. J. Am. Chem. Soc. v.92 A. O. Bedenbaugh;J. H. Bedenbaugh;W. A. Bergin;J. D. Adkins
  33. J. Org. Chem. v.37 H. C. Brown;P. Heim;N. M. Yoon
  34. Chem. Lett. M. Muraki;T. Mukaiyama
  35. Synthesis F. Sato;T. Jinbo;M. Sato
  36. Tetrahedron Lett. T. Fujisawa;T. Mori;S. Tsuge;T. Sato
  37. Zh. Obsch. Khim. v.34 L. I. Zakharkin;I. M. Khorlina
  38. J. Org. Chem. v.49 T. D. Hubert;D. P. Eyman;D. F. Wiemer
  39. Tetrahedron Lett. v.28 J. S. Cha;J. E. Kim;S. Y. Oh;J. D. Kim
  40. Tetrahedron Lett. J. S. Cha;J. E. Kim;M. S. Yoon;Y. S. Kim
  41. J. Am. Chem. Soc. v.92 H. C. Brown;P. Heim;N. M. Yoon
  42. J. Org. Chem. v.38 N. M. Yoon;C. S. Park;H. C. Brown;S. Krishnamurthy;T. P. Stocky
  43. Aldrichimica Acta v.8 C. F. Lane
  44. J. Am. Chem. Soc. v.84 H. C. Brown;A. W. Moerikofer
  45. Inorg. Chem. v.1 H. C. Brown;G. J. Klender
  46. J. Org. Chem. v.41 H. C. Brown;S. Krishnamurthy;N. M. Yoon
  47. J. Am. Chem. Soc. v.93 E. J. Corey;S. M. Albonico;V. Koelliker;T. K. Schaaf;R. K. Varma
  48. J. Org. Chem. v.49 H. C. Brown;C. P. Mathew;C. Pyun;J. C. Son;N. M. Yoon
  49. J. Am. Chem. Soc. v.93 E. J. Corey;S. M. Albonico;V. Koelliker;T. K. Schaaf;R. K. Varma
  50. J. Org. Chem. v.49 H. C. Brown;C. P. Mathew;C. Pyun;J. C. Son;N. M. Yoon
  51. J. Org. Chem. v.41 S. Krishnamurthy;H. C. Brown
  52. Aldrichimia Acta v.7 S. Krishnamurthy
  53. Organic Syntheses via Boranes H. C. Brown;G. W. Kramer;A. B. Levy;M. M. Midland

Cited by

  1. RECENT DEVELOPMENTS IN THE SYNTHESIS OF ALDEHYDES BY REDUCTION OF CARBOXYLIC ACIDS AND THEIR DERIVATIVES WITH METAL HYDRIDES. A REVIEW vol.21, pp.4, 1989, https://doi.org/10.1080/00304948909356413
  2. Conversion of Carboxylic Acids to Aldehydes with Cyclic Dialkyldiaminoaluminum Hydrides vol.23, pp.9, 1988, https://doi.org/10.5012/bkcs.2002.23.9.1340
  3. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1988, https://doi.org/10.5012/bkcs.2011.32.6.1808