1:1 and 1:2 complexes of Bu4NF and BF3·Et2O: Unique properties as reagents for cleavage of silyl ethers

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 509-512

  Kawahara, Shun Ichi ^a   Wada, Takeshi ^a   Sekine, Mitsuo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

THYMIDINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE; THERMODYNAMICS;

EID: 0030033653     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02193-0     Document Type: Article

References (19)

1. a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
2. b) Greene, T. W. and Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley and Sons, Inc.: New York, 1991.
3. a) Corey, E. J.; Venkateswawarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
4. b) Carpino, L. A.; Sau, A. C. J. Chem Soc., Chem. Commun. 1979, 514.
5. d) Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 20, 3981.
6. a) Barton, T. J.; Tully, C. R. J. Org. Chem. 1978, 43, 3649.
7. b) Kelly, D. R.; Robert, S. M. Synthetic Commun. 1979, 9, 295.
8. Corey, E. J.; Yi, K. -L. Tetrahedron Lett. 1992, 33, 2289.
9. a) Pilcher, A. S.; Hill, D. K.; Shimshock, S. J.; Waltermire, R. E.; DeShong, P. J. Org. Chem. 1992, 57, 2492.
10. b) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1993, 58, 5130.
11. Metcalf, B. W.; Bukhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35.
12. 3 varied from 1:0.1 to 1:1.5, were used.
13. Gevorgyan, V.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 7765.
14. 13C NMR. Compounds 1b, 1e, and 1f were synthesized by the literature method: Ogilvie, K. K. Can. J. Chem. 1973, 51, 3799; Ogilvie, K. K.; Donald J. I. Tetrahedron Lett. 1973, 14, 317; Ogilvie, K. K.; Thompson E. A.; Quilliam, M.A.; Westhmore, J. B. Tetrahedron 1974, 33, 2865.
15. 13C NMR. Compounds 1b, 1e, and 1f were synthesized by the literature method: Ogilvie, K. K. Can. J. Chem. 1973, 51, 3799; Ogilvie, K. K.; Donald J. I. Tetrahedron Lett. 1973, 14, 317; Ogilvie, K. K.; Thompson E. A.; Quilliam, M.A.; Westhmore, J. B. Tetrahedron 1974, 33, 2865.
16. 13C NMR. Compounds 1b, 1e, and 1f were synthesized by the literature method: Ogilvie, K. K. Can. J. Chem. 1973, 51, 3799; Ogilvie, K. K.; Donald J. I. Tetrahedron Lett. 1973, 14, 317; Ogilvie, K. K.; Thompson E. A.; Quilliam, M.A.; Westhmore, J. B. Tetrahedron 1974, 33, 2865.
17. 13C NMR. Compounds 1b, 1e, and 1f were synthesized by the literature method: Ogilvie, K. K. Can. J. Chem. 1973, 51, 3799; Ogilvie, K. K.; Donald J. I. Tetrahedron Lett. 1973, 14, 317; Ogilvie, K. K.; Thompson E. A.; Quilliam, M.A.; Westhmore, J. B. Tetrahedron 1974, 33, 2865.
18. Calculation was performed on a Cray C916/12256 super computer by using Guassian 94, Revision B.3: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J.; R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc., Pittsburgh PA, 1995.
19. One of the referees kindly suggested this possibility.