Uncatalysed hydrogen-transfer reductions of aldehydes and ketones

Chemical Communications

Volumn , Issue 3, 1999, Pages 287-288

  Bagnell, Laurence ^a   Strauss, Christopher R ^a  

^a CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HYDROGEN; KETONE;

ARTICLE; HIGH TEMPERATURE; HYDROGENATION; REDUCTION;

EID: 0033531375     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808977i     Document Type: Article

References (23)

1. For classification, see E. A. Braude and R. P. Linstead, J. Chem, Soc., 1954, 3544.
2. Cannizzarro and Tishchenko reactions are exceptions.
3. See the reviews on catalytic transfer hydrogenation: G. Brieger and T. J. Nestrick, Chem. Rev., 1974, 74, 567.; R. A. W. Johnstone, A. H. Wilby and I. D. Entwistle, Chem. Rev., 1985, 85, 129.
4. See the reviews on catalytic transfer hydrogenation: G. Brieger and T. J. Nestrick, Chem. Rev., 1974, 74, 567.; R. A. W. Johnstone, A. H. Wilby and I. D. Entwistle, Chem. Rev., 1985, 85, 129.
5. C. F. de Grauw, J. A. Peters, H. van Bekkum and J. Huskens, Synthesis, 1994, 1007.
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7. R. M. Kellogg, in Comprehensive Organic Synthesis, series ed. B. M. Trost and I. Fleming, vol. ed. I. Fleming, Pergamon, Oxford, 1993, vol. 8, p. 79.
8. iOH or 1-phenylethanol, was reported for catalytic reductions of aldehydes and ketones. See T. Ooi, T. Miura, and K. Maruoka, Angew. Chem. Int. Ed., 1998, 37, 2347.
9. R. A. Sheldon, CHEMTECH, 1994, 24(3), 38.; R. A. Sheldon, Chem. Ind. (London), 1997, 12.
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12. T. Cablewski, A. F. Faux and C. R. Strauss, J. Org. Chem., 1994, 59, 3408.; K. D. Raner, C. R. Strauss, R. W. Trainor and J. S. Thorn, J. Org. Chem., 1995, 60, 2456.; C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665.; J. Li, A. W.-H. Mau and C. R. Strauss, Chem. Commun., 1997, 1275.; L. Bagnell, M. Bliese, T. Cablewski, C. R. Strauss and J. Tsanaktsidis, Aust. J. Chem., 1997, 50, 921.; J. An, L. Bagnell, T. Cablewski, C. R. Strauss and R. W. Trainor, J. Org. Chem., 1997, 62, 2505.
13. T. Cablewski, A. F. Faux and C. R. Strauss, J. Org. Chem., 1994, 59, 3408.; K. D. Raner, C. R. Strauss, R. W. Trainor and J. S. Thorn, J. Org. Chem., 1995, 60, 2456.; C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665.; J. Li, A. W.-H. Mau and C. R. Strauss, Chem. Commun., 1997, 1275.; L. Bagnell, M. Bliese, T. Cablewski, C. R. Strauss and J. Tsanaktsidis, Aust. J. Chem., 1997, 50, 921.; J. An, L. Bagnell, T. Cablewski, C. R. Strauss and R. W. Trainor, J. Org. Chem., 1997, 62, 2505.
14. T. Cablewski, A. F. Faux and C. R. Strauss, J. Org. Chem., 1994, 59, 3408.; K. D. Raner, C. R. Strauss, R. W. Trainor and J. S. Thorn, J. Org. Chem., 1995, 60, 2456.; C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665.; J. Li, A. W.-H. Mau and C. R. Strauss, Chem. Commun., 1997, 1275.; L. Bagnell, M. Bliese, T. Cablewski, C. R. Strauss and J. Tsanaktsidis, Aust. J. Chem., 1997, 50, 921.; J. An, L. Bagnell, T. Cablewski, C. R. Strauss and R. W. Trainor, J. Org. Chem., 1997, 62, 2505.
15. T. Cablewski, A. F. Faux and C. R. Strauss, J. Org. Chem., 1994, 59, 3408.; K. D. Raner, C. R. Strauss, R. W. Trainor and J. S. Thorn, J. Org. Chem., 1995, 60, 2456.; C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665.; J. Li, A. W.-H. Mau and C. R. Strauss, Chem. Commun., 1997, 1275.; L. Bagnell, M. Bliese, T. Cablewski, C. R. Strauss and J. Tsanaktsidis, Aust. J. Chem., 1997, 50, 921.; J. An, L. Bagnell, T. Cablewski, C. R. Strauss and R. W. Trainor, J. Org. Chem., 1997, 62, 2505.
16. T. Cablewski, A. F. Faux and C. R. Strauss, J. Org. Chem., 1994, 59, 3408.; K. D. Raner, C. R. Strauss, R. W. Trainor and J. S. Thorn, J. Org. Chem., 1995, 60, 2456.; C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665.; J. Li, A. W.-H. Mau and C. R. Strauss, Chem. Commun., 1997, 1275.; L. Bagnell, M. Bliese, T. Cablewski, C. R. Strauss and J. Tsanaktsidis, Aust. J. Chem., 1997, 50, 921.; J. An, L. Bagnell, T. Cablewski, C. R. Strauss and R. W. Trainor, J. Org. Chem., 1997, 62, 2505.
17. When this reaction was attempted in MeOH, the dimethyl acetal of cinnamaldehyde resulted.
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