The question of C- Vs. O-silylation of ketenes: Electrophilic triethylsilylation of diphenylketene

Proceedings of the National Academy of Sciences of the United States of America

Volumn 102, Issue 18, 2005, Pages 6251-6254

  Prakash, G K Surya ^a   Bae, Chulsung ^a   Rasul, Golam ^a   Olah, George A ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CATION; DIPHENYL (TRIETHYLSILYL) ACETYL; DIPHENYLKETENE; KETENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON SILYLATION; ELECTROPHILIC TRIETHYLSILYLATION; OXYGEN SILYLATION; PRIORITY JOURNAL; SILYLATION;

EID: 18144415815     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0501813102     Document Type: Article

References (33)

1. Tidwell, T. T. (1995) Ketenes (Wiley, New York).
2. Seikaly, H. R. & Tidwell, T. T. (1986) Tetrahedron 42, 2587-2613.
3. Leung-Toung, R., Peterson, M. R., Tidwell, T. T. & Csizmadia, I. G. (1989) J. Mol. Struct. 183, 319-330.
4. Nobes, R. H., Bouma, W. J. & Radom, L. (1983) J. Am. Chem. Soc. 105, 309-314.
5. Armitage, M. A., Higgins, M. J., Lewars, E. G. & March, R. E. (1980) J. Am. Chem. Soc. 102, 5064-5068.
6. Vogt, J., Williamson, A. D. & Beauchamp, J. L. (1978) J. Am. Chem. Soc. 100, 3478-3483.
7. Traeger, J. C., McLoughlin, R. G. & Nicholson, A. J. C. (1982) J. Am. Chem. Soc. 104, 5318-5322.
8. Hopkinson, A. C. (1973) J. Chem. Soc. Perkin Trans. 2 795-797.
9. Allen, A. D. & Tidwell, T. T. (1991) Tetrahedron Lett. 32, 847-850.
10. Allen, A. D., Stevenson, A. & Tidwell, T. T. (1989) J. Org. Chem. 54, 2843-2848.
11. Allen, A. D. & Tidwell, T. T. (1987) J. Am. Chem. Soc. 109, 2774-2780.
12. Allen, A. D., Kresge, A. J., Schepp, N. P. & Tidwell, T. T. (1987) Can. J. Chem. 65, 1719-1723.
13. Kabir, S. H., Seikaly, H. R. & Tidwell, T. T. (1979) J. Am. Chem. Soc. 101, 1059-1060.
14. Olah, G. A., Alemayehu, M., Wu, A., Farooq, O. & Prakash, G. K. S. (1992) J. Am. Chem. Soc. 114, 8042-8045.
15. Corey, J. Y. (1975) J. Am. Chem. Soc. 97, 3237-3238.
16. Lambert, J. B., Zhang, S., Stern, C. L. & Huffman, J. C. (1993) Science 260, 1917-1918.
17. Prakash, G. K. S., Bae, C., Wang, Q., Rasul, G. & Olah, G. A. (2000) J. Org. Chem. 65, 7646-7649.
18. Steinberger, H.-U., Muller, T., Auner, N., Maerker, C. & Schleyer, P. von R. (1997) Angew. Chem. Int. Ed. Engt. 36, 626-628.
19. Bahr, S. R. & Boudjouk, P. (1993) J. Am. Chem. Soc. 115, 4514-4519.
20. Olah, G. A., Li, X.-Y., Wang, Q., Rasul, G. & Prakash, G. K. S. (1995) J. Am. Chem. Soc. 117, 8962-8966.
21. Prakash, G. K. S., Bae, C., Rasul, G. & Olah, G. A. (2002) J. Org. Chem. 67, 1297-1301.
22. Frainnet, É. & Caussé, J. (1968) Bull. Soc. Chim. Fr. 3034-3036.
23. Hertenstein, U., Hünig, S., Reichelt, H. & Schaller, R. (1982) Chem. Ber. 115, 261-287.
24. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, J. A., Stratmann, R. E. & Burant, J. C., et al. (1998) GAUSSIAN 98 (Gaussian, Pittsburgh), Revision A.5.
25. Foresman, J. B. & Frisch, A. (1995) Exploring Chemistry with Electronic Structure Methods (Gaussian, Pittsburgh), p. 64.
26. Kutzelnigg, W. (1980) Isr. J. Chem. 19, 193-195.
27. Huzinaga, S. (1971) Approximate Atomic Wave Function (Univ. of Alberta, Edmonton, AB, Canada).
28. Olah, G. A. & White, A. M. (1969) J. Am. Chem. Soc. 91, 5801-5810.
29. Siehl, H.-U., Kaufmann, F.-P., Apeloig, Y., Braude, V., Danovich, D., Berndt, A. & Stamatis, N. (1991) Angew. Chem. Int. Ed. Engl. 30, 1479-1482.
30. Siehl, H.-U. & Kaufmann, F.-P. (1992) J. Am. Chem. Soc. 114, 4937-4939.
31. Prakash, G. K. S., Reddy. V. P., Rasul, G., Casanova, J. & Olah, G. A. (1992) J. Am. Chem. Soc. 114, 3076-3078.
32. Lambert, J. B., Zhao, Y. & Wu, H. (1999) J. Org. Chem. 64, 2729-2736.
33. Muller, T., Meyer, R., Lennartz, D. & Siehl, H.-U. (2000) Angew. Chem. Int. Ed. 39, 3074-3077.