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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 4
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Original Articles

Deoxygenation of Aldehydes and Ketones: An Improved Procedure

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Pages 275-279 | Received 27 Sep 1978, Published online: 05 Dec 2006

References

  • Kabalka , G. W. and Baker , J. D. Jr. 1975 . J. Org. Chem. , 40 : 1834
  • Kabalka , G. W. , Yang , D. T. C. and Baker , J. D. Jr. 1976 . J. Org. Chem. , 41 : 574
  • Yang , D. T. C. and Kabalka , G. W. 1977 . Org. Prep. Proced. Int. , 9 : 85
  • Kabalka , G. W. , Chandler , J. H. , Newton , R. J. Jr. and Yang , D. T. C. Chem. Commun. , in press
  • Hutchins , R. O. , Milewski , G. and Maryanoff , B. 1973 . J. Am. Chem. Soc. , 95 : 3662
  • Caglioti , L. 1966 . Tetrahedron , 22 : 487
  • Hutchins , R. O. , Kacher , M. and Rua , L. 1975 . J. Org. Chem. , 40 : 923
  • Kabalka , G. W. , Baker , J. D. Jr. and Neal , G. W. 1977 . J. Org. Chem. , 42 : 512
  • Kabalka , G. W. , Yang , D. T. C. , Chandler , J. H. and Baker , J. D. Jr. 1977 . Synthesis , : 124
  • 1968 . Indian J. Chem. , 6 : 718 Tetramethylammonium acetate C. A., 70, 81570(1969)] was also prepared. It is relatively insoluble in chloroform and the yields obtained in reductions using this base were only slightly greater than those obtained using sodium acetate. This observation supports the postulation that the addition of dimethyl sulfoxide to the decomposition reactions using sodium acetate increases the yield by solubilizing the sodium acetate rather than by providing an alternate reaction pathway
  • The excess catecholborane was added to achieve a convenient reduction rate. Alternately, the reduction may be achieved by utilizing one equivalent of catecholborane and longer reaction times. In general, the yields of the overall sequence reflect the yields obtained in the reduction step. It is advisable to monitor the reduction (by NMR) until the tosylhydrazone is reduced. The reduction times are sensitive to the substrate and vary from minutes to days (for acetylenic tosylhydrazones.)

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