Efficient, general synthesis of silylketenes via an unusual rhodium mediated Wolff rearrangement

Chemical Communications

Volumn , Issue 13, 1999, Pages 1199-1200

  Marsden, Stephen P ^a   Pang, Wai Kit ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

KETENE DERIVATIVE; RHODIUM; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; SYNTHESIS;

EID: 0033532916     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902549i     Document Type: Article

References (13)

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3. S. P. Marsden and W.-K. Pang, Tetrahedron Lett., 1998, 39, 6077.
4. S. N. Kablean, S. P. Marsden and A. M. Craig, Tetrahedron Lett., 1998, 39, 5109.
5. All of the silyl diazo ketones were prepared by C-silylation of the corresponding diazo ketones with triethylsilyl triflate, according to: T. Allspach, H. Gümbel and M. Regitz, J. Organomet. Chem., 1985, 290, 33.
6. (a) G. Maas and R. Brückmann, J. Org. Chem., 1985, 50, 2801;
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10. S. Bien and Y. Segal, J. Org. Chem., 1977, 42, 1685; G. B. Gill, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 88.
11. S. Bien and Y. Segal, J. Org. Chem., 1977, 42, 1685; G. B. Gill, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 3, p. 88.
12. The rhodium catalysed decomposition of ethyl (E)-5-aryl-2-diazo-3-oxopent-4-enoates results in products assumed to arise via Wolff rearrangement and ketene decomposition. See: E. C. Taylor and H. M. L. Taylor, Tetrahedron Lett., 1983, 24, 5453.
13. E. Colvin, Silicon in Organic Synthesis, Butterworths, London, 1981.