Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 15, 1985 - Issue 11
340
Views
34
CrossRef citations to date
0
Altmetric
Original Articles

Allylic Alcohols Via the Chemoselective Reduction of Enone Systems with Sodium Borohydride in Methanolic Tetrahydrofuran

&
Pages 985-990 | Published online: 19 Dec 2006

References

  • Kim , S. and Ahn , K. H. 1984 . J. Org. Chem. , 49 : 1717 S. Kim, Y. C. Moon and K. H. Ahn, J. Org. Chem., 47, 3310 (1982); A. M. Caporusso, G. Giacomelli and L. Lardicci, J. Org. Chem., 47, 4640 (1982); T. Sato, Y. Gotoh, Y. Wakabayashi and T. Fujisawa, Tetrahedron Lett., 24, 4123 (1983) and references cited therein.
  • Brown , H. C. and Krishnamurthy , S. 1979 . Tetrahedron , 35 : 567
  • Johnson , M. R. and Rickborn , B. 1970 . J. Org. Chem. , 35 : 1041
  • Gemal , A. L. and Luche , J.-L. 1981 . J. Am. Chem. Soc. , 103 : 5454 and references cited therein
  • Adams , C. 1984 . Synth. Commun. , 14 : 1349
  • Varma , R. S. and Kabalka , G. W. 1985 . Synth. Commun. , 15 : 151
  • Soai , K. , Oyamada , H. , Takase , M. and Ookawa , A. 1984 . Bull. Chem. Soc. Jpn. , 57 : 1948
  • Lavrushin , V. F. , Kutsenko , L. M. , Grin , L. M. and Litvin , I. Y. 1968 . Ukr. Khim. Zh. , 34 : 413 Chem. Abstr., 69, 76794g (1968); L. M. Grin, L. M. Kutsenko and V. F. Lavrushin, Vest. Kharkov Univ., 46, 81 (1970); Chem. Abstr. 75, 140426s (1971).
  • Wigfield , D. C. and Gowland , F. M. 1976 . Tetrahedron Lett. , 22 : 3373
  • The reaction appears to be general for acyclic systems. In the case of cyclic enones, reduction to the saturated alcohol is also observed e. g. 2-cyclohexen-1-on also produces cyclohexanol (37%) in addition to 2-cyclohexen-1-ol (63%).
  • Huls , R. and Simon , Y. 1956 . Bull. Soc. Roy. Sci. Liege , 25 : 89 Chem. Abst., 50, 16664h (1956).
  • Lutz , R. E. and Weiss , J. O. 1955 . J. Am. Chem. Soc. , 77 : 1814
  • Braude , E. A. and Waight , E. S. 1953 . J. Chem. Soc. , 419
  • Reich , H. J. , Chow , F. and Shah , S. K. 1979 . J. Am. Chem. Soc. , 101 : 6638
  • Hesse , G. , Bayer , E. and Thieme , P. 1966 . Chem. Ber. , 99 : 1810
  • Varma , R. S. , Kabalka , G. W. , Evans , L. T. and Pagni , R. M. 1985 . Synth. Commun. , 15 : 000

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.