Revisiting the reduction of di-tert-butyl ketone with alkali metals

European Journal of Organic Chemistry

Volumn , Issue 12, 2003, Pages 2229-2232

  Bucher, Götz ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

Author keywords

Density functional theory; Ketone dianions; Pinacol coupling; Radical anions; Steric hindrance

Indexed keywords

2,5,5 TRI TERT BUTYL 3 METHYL 4,5 DIHYDROFURAN; ALKALI METAL; DI TERT BUTYL KETONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REDUCTION;

EID: 0037716291     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200200584     Document Type: Article

References (19)

1. L. Eberson, Acta Chem. Scand. 1964, 18, 1255-1260.
2. P. D. Bartlett, T. T. Tidwell, W. P. Weber, Tetrahedron Lett. 1970, 33, 2919-2921.
3. P. G. Stevens, J. H. Mowat, J. Am. Chem. Soc. 1942, 64, 554-556.
4. S. Selman, J. F. Eastham, J. Org. Chem. 1965, 30, 3804-3809.
5. [5a] It is noted that Bartlett, Tidwell, and Weber used a 2.5-fold excess of potassium metal, which may account for their finding of dianion-derived products.
6. [5b] The yields of other constituents of the product mixture (mainly unchanged 1, di-tert-butylmethanol, diol 3, in addition to some minor products, which were not further characterized) were determined by GC and were found to be in agreement with the yields reported by Eberson, see ref.
7. H. Hopf, in Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, pp. 138-150.
8. [7a] A. Krebs, W. Born, B. Kaletta, W.-U. Nickel, W. Rüger, Tetrahedron Lett. 1983, 24, 4821-4823.
9. [7b] A. Krebs, W.-U. Nickel, L. Tikwe, J. Kopf, Tetrahedron Lett. 1985, 26, 1639-1642.
10. [7c] T. Loerzer, R. Gerke, W. Lüttke, Tetrahedron Lett. 1983, 24, 5861-5864.
11. [7d] J. Deuter, H. Rodewald, H. Irngartinger, T. Loerzer, W. Lüttke, Tetrahedron Lett. 1985, 26, 1031-1034.
12. [7e] G. J. Abruscato, T. T. Tidwell, J. Org. Chem. 1972, 37, 4151-4156.
13. H. Hopf, R. Hänel, Chem. Ber. 1994, 127, 2347-2348.
14. A. Bienvenue, B. Duchatellier, Tetrahedron 1972, 28, 833-843.
15. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
16. D. H. Eargle, Jr., R. Emrich, J. Org. Chem. 1970, 35, 3744-3747.
17. In their experiment, Bartlett and co-workers performed the reduction of 1 in the presence of benzene and ethylene, both of which remove the dianion from the equilibrium.
18. R. Knorr, A. Donhärl, K.-O. Hennig, Liebigs Ann. 1996, 155-157.
19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, Jr., M. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Menucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Ciolowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaroni, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.6, Gaussian Inc., Pittsburgh, PA, 1998.