Synthesis and reactivity of silyl vinylketenes: A formal interrupted Dötz benzannulation with unexpected silyl migration

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3389-3391

  Moser, William H ^a   Sun, Liangdong ^a   Huffman, John C ^b  

^a INDIANA UNIVERSITY   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012145090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016615y     Document Type: Article

References (19)

1. For reviews of the Dötz benzannulation, see: (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
2. (b) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12.
3. (c) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, A. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12.
4. (d) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
5. (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1979, 18, 954.
6. (b) Dötz, K. H.; Fügen-Köster, B. Chem. Ber. 1980, 113, 1449.
7. (c) Wulff, W. D.; Tang, P.-C. J. Am. Chem. Soc. 1984, 106, 1132.
8. (d) Wulff, W. D.; Xu, Y.-C. J. Org. Chem. 1987, 52, 3263.
9. Huang, W.; Tidwell, T. T. Synthesis 2000, 457 and references therein.
10. (a) Pommier, A.; Kocienski, P.; Pons, J. J. Chem. Soc., Perkin Trans. 1 1998, 2105.
11. (b) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.
12. (c) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9690.
13. (d) Bennett, D. M.; Okamoto, I.; Danheiser, R. L. Org. Lett. 1999, 1, 641.
14. Dötz, K. H.; Mühlemeier, J.; Trenkle, B. J. Organomet. Chem. 1985, 289, 257.
15. Crystallographic data can be found in the Supporting Information.
16. Waters, M. L.; Brandvold, T. A.; Isaacs, L.; Wulff, W. D.; Rheingold, A. L. Organometallics 1998, 17, 4298.
17. Isomerizations of this type are well documented for bis-silyl ketenes and silyl allenylketenes and by analogy are presumed to take place through a reversible 4π electrocyclic ring closure. Further details of this process will be reported elsewhere.
18. a) Chamberlin, S.; Wulff, W. D. J. Org. Chem. 1994, 59, 3047.
19. (b) Fogel, L.; Hsung, R. P.; Wulff, W. D.; Sommer, R. D.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 5580.