Silicon migration from oxygen to carbon and decarbonylation in methoxytriphenylsiloxycarbene

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2733-2736

  Pezacki, John Paul ^a   Loncke, Paul G ^b   Ross, Joseph P ^a   Warkentin, John ^a   Gadosy, Timothy A ^b  

^a MCMASTER UNIVERSITY   (Canada)

^b Dept of Electrical and Computer Engineering   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000963932     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006117+     Document Type: Article

References (42)

1. Warkentin, J. In Advances in Carbene Chemistry, Vol. 2; Brinker, U., Ed.; JAI Press Inc.: Greenwich, 1998; pp 245-295.
2. (a) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1264.
3. (b) Couture, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1281.
4. (c) Kassam, K.; Venneri, P.; Warkentin, J. Can. J. Chem. 1997, 75, 1256.
5. (d) Kassam, K.; Warkentin, J. Can. J. Chem. 1997, 75, 120.
6. (e) Kassam, K.; Warkentin, J. J. Org. Chem. 1994, 59, 5071.
7. (f) Er, H.-T.; Pole, D. L.; Warkentin, J. Can. J. Chem. 1996, 74, 1480.
8. (a) Pezacki, J. P.; Pole, D. L.; Warkentin, J.; Chen, T.; Ford, F.; Toscano, J.; Fell, J.; Platz, M. S. J. Am. Chem. Soc. 1997, 119, 3191.
9. (b) Pezacki, J. P.; Wood, P. D.; Gadosy, T. A.; Lusztyk, J.; Warkentin, J. J. Am. Chem. Soc. 1998, 120, 8681.
10. (c) Pezacki, J. P.; Warkentin, J.; Wood, P. D.; Lusztyk, J.; Yuzawa, T.; Gudmundsdottir, A. D.; Morgan, S.; Platz, M. S. J. Photochem. Photobiol. A: Chem. 1998, 116, 1.
11. (d) Pezacki, J. P.; Couture, P.; Dunn, J. A.; Warkentin, J.; Wood, P. D.; Lusztyk, J.; Ford, F.; Platz, M. S. J. Org. Chem. 1999, 64, 4456.
12. (e) Tae, E. L.; Zhu, Z.; Platz, M. S.; Pezacki, J. P.; Warkentin, J. J. Phys. Chem. A 1999, 103, 5336.
13. For a review of α-siloxycarbenes generated from acylsilanes, see: Brook, A. G. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1989; Chapter 15, pp 984-988. Also see: (a) Brook, A. G.; Kucera, H. W.; Pearce, R. Can. J. Chem. 1971, 49. 1618.
14. For a review of α-siloxycarbenes generated from acylsilanes, see: Brook, A. G. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley and Sons: New York, 1989; Chapter 15, pp 984-988. Also see: (a) Brook, A. G.; Kucera, H. W.; Pearce, R. Can. J. Chem. 1971, 49. 1618.
15. (b) Duff, J. M.; Brook, A. G. Can J. Chem. 1973, 51, 2869.
16. (c) Bourque, R. A.; Davis, P. D.; Dalton, J. C. J. Am. Chem. Soc. 1981, 103, 697.
17. (a) Pole, D. L.; Sharma, P. K.; Warkentin, J. Can. J. Chem. 1996, 74, 1335.
18. (b) Kirmse, W.; Guth, M.; Steenken, S. J. Am. Chem. Soc. 1996, 118, 10838.
19. (c) González, R.; Wudl, F.; Pole, D. L.; Sharma, P. K.; Warkentin, J. J. Org. Chem. 1996, 61, 5837.
20. (d) Kirmse, W.; Konrad, W.; Schnitzler, D. J. Org. Chem. 1994, 59, 3821.
21. (e) Walsh, R.; Wolf, C.; Untiedt, S.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 421.
22. (f) Walsh, R.; Untiedt, S.; de Meijere, A. Chem. Ber. 1994, 127, 237.
23. (g) Shimizu, H.; Gordon, M. S.; Organometallics 1994, 13, 186.
24. (h) Barton, T. J.; Lin, J.; Ijadi-Maghsoodi, S.; Power, M. D.; Zhang, X.; Ma, Z.; Shimuzu, H.; Gordon, M. S. J. Am. Chem. Soc. 1995, 117, 11695.
25. (i) Creary, X.; Wang, Y.-X. J. Org. Chem. 1994, 59, 1604.
26. Baird, M. S.; Dale, C. M.; Al Dulayymi, J. R. J. Chem. Soc., Perkin Trans. 1 1993, 1373.
27. Kassam, K.; Pole, D. L.; El-Saidi, M.; Warkentin, J. J. Am. Chem. Soc. 1994, 116, 1161.
28. (a) Brook, A. G. J. Am. Chem. Soc. 1955, 77, 4827.
29. (b) Brook, A. G.; Mauris, R. J. J. Am. Chem. Soc. 1957, 79, 971.
30. It is well established that other metallo formates containing Sn, Se, or Te can undergo thermal or photochemical M-C bond homolysis to give acyl radical/metal radical pairs. Acyl radicals then can undergo either decarboxylation or decarbonylation. See: Lucas, M. A.; Schiesser, C. H. J. Org. Chem. 1996, 61, 5754 and references therein.
31. Some dialkoxycarbenes fragment in solution to radical pairs. See: (a) Venneri, P. C.; Warkentin, J. J. Am. Chem. Soc. 1998, 120, 11182.
32. (b) Merkley, N.; El-Saidi, M.; Warkentin, J. Can. J. Chem. 2000, 78, 356.
33. (c) Reid, D. L.; Hernández-Trujillo, J.; Warkentin, J. J. Phys. Chem. A 2000, 104, 3398.
34. (a) Du, X.-M.; Fan, H.; Goodman, J. L.; Kesselmayer, M. A.; Krogh-Jespersen, K.; LaVilla, J. A.; Moss, R. A.; Shen, S.; Sheridan, R. S. J. Am. Chem. Soc. 1990, 112, 1920.
35. (b) Moss, R. A.; Wlostowski, M.; Shen, S.; Krogh-Jespersen, K.; Matro, A. J. Am. Chem. Soc. 1988, 110, 4443.
36. Couture, P.; El-Saidi, M.; Warkentin, J. Can. J. Chem. 1997, 75, 326.
37. Suh, D.; Pole, D. L.; Warkentin, J.; Terlouw, J. K. Can. J. Chem. 1996, 74, 544.
38. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, Cammi, M.; Mennucci, R.; B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7, Gaussian, Inc.: Pittsburgh, PA, 1998.
39. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899.
40. Moss, R. A.; Xue, S.; Liu, W.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1996, 118, 12588.
41. Moss, R. A. Acc. Chem. Res. 1999, 32, 9691 and references therein.
42. Yan, S.; Sauers, R. R.; Moss, R. A. Org. Lett. 1999, 1, 1603.